The Official SaaStr Podcast: SaaS | Founders | Investors

By SaaStr

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 Mar 14, 2019

Description

he Official SaaStr Podcast is the latest and greatest from the world of SaaStr, interviewing the most prominent operators and investors to discover their tips, tactics and strategies to attain success in the fiercely competitive world of SaaS. On the side of the operators, we center around getting from $0 to $100m ARR faster, what it takes to scale successfully and what are the core elements of hiring. As for the investors, we learn what metrics they hone in on when examining SaaS business, what type of metrics excites them and what they look for in SaaS founders.

Episode Date
SaaStr 430: The Secrets to $1B ARR and 100,000 Happy Customers with Brian Halligan, CEO and Co-Founder @ HubSpot, and Jason Lemkin, CEO and Founder @ SaaStr
38:43

In today’s SaaStr insider episode, SaaStr CEO and Founder, Jason Lemkin catches up with Brian Halligan, CEO and Co-founder of HubSpot. Together they discuss: why partners are a moat, why HubSpot avoided going more enterprise, building vs. buying, and building an eco-system. 

Feb 19, 2021
SaaStr 429: The Current State of SaaS Companies, Subscriptions, and Retention in 2021 with Patrick Campbell, Founder & CEO @ ProfitWell
27:02

In this episode, ProfitWell Founder & CEO Patrick Campbell shares benchmarks from over 23,000 companies and offers a helpful framework to re-evaluate your retention strategy and increase your CLV (Customer Lifetime Value) between 10 and 60%.

Feb 18, 2021
SaaStr 428: How to Execute a Winning Self-Service Strategy with Naomi Rozenfeld, VP of Revenue @ Wix Answers, and Amelia Ibarra, SVP & GM @ SaaStr 
44:15

In today's SaaStr insider episode, SaaStr SVP and GM, Amelia Ibarra sits down with Naomi Rozenfeld, VP of Revenue @ Wix Answers. Together they discuss how to execute a winning self-service strategy, including when to launch, cross-functional implications, and how to find the right balance between self-service and customer support.

Feb 12, 2021
SaaStr 427: How to Build a Great Intern Program with Farhan Thawar, VP Engineering @ Shopify
25:13

Internships have sparked millions of successful careers, and they can be a valuable talent pool from which companies can eventually hire full-time employees. But it’s critical to build your internship program the right way. Farhan Thawar, the VP of Engineering at Shopify, has dedicated years to perfecting his internship program and shares his insider tips for launching a successful initiative of your own.

Feb 11, 2021
SaaStr 426: How to Market at Mass Scale, with Harry Stebbings and Ryan Bonnici, CMO @ Whereby
39:12

In today's SaaStr insider episode, Harry Stebbings sits down with Ryan Bonnici, Chief Marketing Officer at Whereby to chat about how to market at scale.

Together, they cover how to hire marketers at scale and how to use marketing to set your brand above the rest.

Feb 08, 2021
SaaStr 425: 5 Interesting Learnings from Atlassian at $2B in ARR with SaaStr CEO and Founder, Jason Lemkin
18:12

Atlassian has always done things a bit differently.  With a relatively small sales team and a huge investment in R&D since inception, Atlassian is proof that you can build a decacorn from anywhere.

Listen in to the 5 Interesting learnings we can take away from Atlassian at $2B in ARR.

Feb 05, 2021
SaaStr 424: How To Raise Your Next Round. What It Takes to Really Raise Capital in 2021 with Christoph Janz, Co-Founder and Partner @ Point Nine Capital
26:47

Each year, Point 9 Capital surveys founders and investors to explore what it takes to raise capital for SaaS companies. In this episode, Christoph Janz, a Founding Partner at Point 9 Capital, gives his data-backed insight into what investors are looking for in the year ahead. 

Feb 04, 2021
SaaStr 423: The Misunderstanding of Enterprise Marketing and What it Really Takes to Scale with Menaka Shroff, Director of Marketing @ Google 
21:53

When you’re ready to take your enterprise marketing to the next level, you may run into some common pitfalls that hinder optimal performance. In this episode, Menaka Shroff, the Director of Global Marketing at Google, shares her observations of the misunderstandings she has seen during her career and how to avoid them.

Feb 01, 2021
SaaStr 422: The Twists and Turns Along the Way to Building a Unicorn with SalesLoft CEO, Kyle Porter, and SaaStr CEO and Founder, Jason Lemkin
56:26

After a newly minted $1.1B valuation, Kyle Porter, CEO of SalesLoft, sits down with SaaStr CEO and Founder, Jason Lemkin to talk about the twists and turns along the way to building SalesLoft into the Unicorn it is today. From completely pivoting the product early on, to becoming an essential software tool for inside sales reps -- learn how SalesLoft landed some of the Cloud giants like Shopify, Google, and Slack as its customers, and what it takes to build a Unicorn company in today's changing market. 

Jan 29, 2021
SaaStr 421: 11 tips to Build Stronger Relationships with Customers with Jason Lemkin, CEO @ SaaStr
16:41

One of the easiest ways to consistently grow revenue is to make your customers happier. They buy more and churn less when you do. Here are 11 actionable steps and tips that always work in SaaS companies to drive NPS and happiness up from SaaStr CEO & Founder Jason Lemkin. 

Jan 22, 2021
SaaStr 420: Mastering the Art and Science of Product-Led Growth with Mickey Alon, Founder, and CTO @ Gainsight PX and Ciara Peter, VP, Product @ Gainsight
26:03

Product-led growth is a disruptive go-to-market strategy adopted by the most successful companies in the subscription business, including Slack, Dropbox, Twilio, and Shopify. Drawing on his personal experience building innovative SaaS products, Mickey Alon, the creator of Gainsight PX, and Ciara Peter, VP Product at Gainsight, will cover the principles of Product-led growth strategy, how to build a product growth team, and how product teams can apply this strategy as part of their 2021 roadmap.

Jan 21, 2021
SaaStr 419: How To Collaborate, Manage & Work with Developers with Jeff Lawson, CEO and Co-Founder @ Twilio and Jason Lemkin, CEO @ SaaStr
53:19

At his core, Jeff Lawson is a software developer first, and a CEO second. He knows both sides of the executive & engineering equation intimately. He gets what goes on in a developer's brain and the detailed process of building software, but he understands that businesses are motivated to move quickly. And in turn, developers need to adapt.

An all-time SaaStr fan-favorite, Jeff recently chatted with SaaStr CEO Jason Lemkin to discuss his thoughts on collaborating, managing, and working with developers.

Jan 15, 2021
SaaStr 418: 10 Rules for Defining Churn with Andrea Webb, SVP of Customer Success & Retention @ Solarwinds, and Tim Willey, the SVP of Commercial Strategy & Operations @ ForgeRock
25:55

Reducing churn in SaaS, along with increasing new ARR is the backbone to growing your business. In this guide, Andrea Webb, the SVP of Customer Success & Retention at Solarwinds, and Tim Willey, the SVP of Commercial Strategy & Operations at ForgeRock, share their tips for understanding and combating churn. 

Jan 14, 2021
SaaStr 417: How Sales and Product Really Should Work Together with Javier Molina, VP, Corporate Sales, Americas @ MongoDB and Sahir Azam, Chief Product Officer @ MongoDB
54:45

In this episode, Sahir Azam, Chief Product Officer at MongoDB, and Javier Molina, SVP at MongoDB, share their journey to increasing company revenue through their cohesive sales and product relationship. When sales and product work together, amazing things happen.

Jan 08, 2021
SaaStr 416: The Secret Sauce for Scaling to $1B with Sharon Prosser, VP, Global SMB GTM and Business Development @ Zendesk, and Astha Malik, VP, GTM Strategy, Planning and Enablement @ Zendesk
21:52

As your company grows, so does the focus on enterprise deals. Learn from Zendesk senior management about how to balance your needs and organization’s focus on enterprise wins to reach $1B in revenue without ever forgetting the importance of catering to your original customer base and extending those learnings into new market segments.

Jan 07, 2021
SaaStr 415: Fighting Churn with Data featuring, Carl Gold, Chief Data Scientist @ Zuora 
45:12

Customer churn is the bane of online businesses, and data can help you understand the causes of churn and take action to reduce it. In this podcast, you'll discover powerful customer metrics that help your entire organization. 

Jan 01, 2021
SaaStr 414: How to Leverage the Cloud Giants to Scale to 100 Million ARR and Beyond with Snowflake, CrowdStrike, Sumo Logic, and Sapphire Ventures
25:50

To help revenue and sales leaders navigate and identify ways to leverage cloud marketplaces, join Sapphire Ventures, Snowflake, Tackle.io, and Crowdstrike to understand: How to successfully sell enterprise software through the major cloud marketplaces, what investments and alignment you need at your company need to be successful transacting on cloud marketplaces, and how to cultivate and enable a successful co-sell relationship with cloud marketplaces.

Dec 31, 2020
SaaStr 413: How to Build a Unicorn in 8 Simple Steps with Auren Hoffman, CEO @ SafeGraph
51:50

Join four-time Founder and CEO Auren Hoffman as he breaks down how businesses can become the right model for explosive growth, emulate their strategy, and join the path to Unicorn potential in eight simple, hand-made steps.

Dec 29, 2020
SaaStr 412: The Secrets to Turbocharging Sales in 2021 with Keyfactor, Checkout.com, Contentstack, and Insight Partners
29:40

2020 has been a wild ride, but Sales teams are still expected to deliver. Hear from 3 companies on how they delivered in a year riddled with challenges, and what those battle scars have taught them as they plan to turbocharge their sales in 2021. Walk away from this episode with the tactics and tips you and your Sales team need for the upcoming year.

Dec 24, 2020
SaaStr 411: Slack Chief Product Officer Tamar Yehoshua on Effective Product Design, Customer Development Processes and Evolving Management Philosophies
32:39

Tamar Yehoshua is the Chief Product Officer @ Slack, the company providing a place where people get work done, together. Prior to their direct listing in June 2019, Slack raised over $1.3Bn from the likes of Accel, Thrive, Softbank, Kleiner, IVP, T Rowe, GV, and a16z to name a few. As for Tamar, previously, Tamar was a Vice President at Google, holding product and engineering leadership roles on Google’s most important products, including Search, Identity, and Privacy. Prior to that, she was the Vice President of Advertising Technologies at Amazon’s A9. If that was not enough Tamar is also on the board of 2 public companies in the form of Yext and ServiceNow.

 In Today’s Episode We Discuss:

  • How Tamar made her way from Google and Amazon into the world of bottoms up SaaS with one of the leading companies of our generation, Slack?
  • What were Tamar’s biggest takeaways from her time with Amazon and Google? How did Jeff Bezos’ approach to “the customer” impact Tamar’s operating mindset? How does Tamar analyse customer responses to product changes? How important a role does the press play in customer’s responses? 
  • How does Tamar think about effective product design today? How does Tamar structure the customer development process? What questions does she ask? What is she looking for? Where do many people go wrong with customer discovery? What channels can teams put in place to have this real-time dialogue with their customers?        
  • How would Tamar describe her management philosophy today? What have been some of Tamar’s biggest lessons on giving effective feedback? How should it be structured? When should it be given? To what extent does Tamar agree with “radical candour”? Where do many go wrong in giving their feedback?

Tamar’s 60 Second SaaStr:

  1. The most challenging element of Tamar’s role with Slack?
  2. What would Tamar most like to change about the SaaS industry?
  3. What moment in Tamar’s life has served as an inflection point and changed the way she thinks? 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Dec 22, 2020
SaaStr 410: 10x Your Organization's Performance with Todd McKinnon, CEO and Co-Founder @ Okta and Jason Lemkin, CEO @ SaaStr
52:55

In today's SaaStr insider episode SaaStr CEO and Founder Jason Lemkin catches up with Todd McKinnon, CEO and co-founder of Okta. Together they discuss what it takes to build, maintain and grow a high-performance organization

Dec 20, 2020
SaaStr 409: Lessons in Scaling a Low Code Platform with Howie Liu, Co-Founder, and CEO @ Airtable
26:16

As one of the early champions of "low-code”, Howie Liu shares the lessons he's learned building and scaling a company in an entirely new category. He'll discuss how Airtable focuses on solving customers' increasingly complex needs, all with products that are easily adoptable.

Dec 18, 2020
SaaStr 408: Going Long and the 20-year Journey of Being a CEO + Founder with Therese Tucker, CEO and Founder @ BlackLine and Jason Lemkin, CEO and Founder @ SaaStr
41:49

SaaStr CEO and Founder Jason Lemkin catches up with Therese Tucker, Founder, and CEO at BlackLine about her SaaS journey, going long and surviving black swan events.

Dec 11, 2020
SaaStr 407: The Secrets of Market Timing and How to Develop the Right Idea, at the Right Time with Allen Gannett, Author of the Creative Curve
22:04

Trends are fleeting and hard to pin down. Or are they? Learn how you can leverage the science of trends and better understand market behavior. 

Dec 10, 2020
SaaStr 406: Notion's Head of Customer Experience, Kate Taylor on How To Approach Delegation at Scale, How Leaders Can Truly Empower Their Team Members & The Role of Sales in a World of Product-Led Growth
29:33

Kate Taylor is Head of Customer Experience at Notion, one of the fastest-growing startups of the last 5 years with over $68M in funding from some of the best in the business including Index, Daniel Gross, Elad Gil, Lachy Groom, Josh Kopelman and Aydin Senkut to name a few. As for Kate, prior to making the move to Notion just last month, she spent an incredible 8 years at Dropbox including holding roles such as Head of Sales Development, North America and Director of Global SMB Revenue and Operations. Before Notion, Kate spent 2 years at Salesforce in the corporate sales and enterprise business units. 

 In Today’s Episode We Discuss:

  • How Kate made her way into the world of SaaS with Salesforce, how that led to her 8 year tenure at Dropbox before joining the breakout, Notion?
  • Why does Kate not believe that in startups you can “do it all”? How to discover the problems people care about? How to think through prioritisation of problems at the early stage? Where do many people make mistakes here?
  • How does Kate approach delegation at scale? When is the right time to start? How can founders let go and entrust others to do the role they have been doing? How can leaders build trust with the people they work with? How can leaders empower employees with act with conviction and invest in them?        
  • What is the role of sales in a product-led growth organisation? How can sales and product work effectively well together? Where do many mistakes happen in sales and product? How can product and marketing also collaborate productively? What can one do to shorten the feedback cycles as much as possible?

Kate’s 60 Second SaaStr:

  1. Most challenging element of Kate’s role with Notion?
  2. What would Kate like to change about the world of SaaS?
  3. What does Kate know now that she wishes she had known from the beginning? 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Dec 08, 2020
SaaStr 405: 6 Learnings on Scaling to $100M ARR with Bernadette Nixon, CEO @ Algolia and Jason Lemkin, CEO @ SaaStr
39:27

In today's SaaStr insider episode SaaStr CEO and Founder Jason Lemkin catches up with Bernadette Nixon CEO at Algolia and together they share 6 learnings on scaling to $100M ARR and what it really takes selling to customers small, medium and large.

Dec 04, 2020
SaaStr 404: The Secrets To Managing in All Directions with Arquay Harris, Sr. Director Engineering @ Slack
27:57

The benefits of managing upwards and downwards are frequent management topics. However, managing sideways and inward are also important skills for a successful leader. Learn new ways to build strong teams by managing in all directions from Arquay Harris at Slack.

Dec 03, 2020
SaaStr 403: Loom's VP Sales, Sam Taylor on Sales' Role in a Product-Led-Growth Organisation, How Sales Can Most Effectively Work With Marketing & When To Hire Your First Reps When Selling Bottoms Up
34:23

Sam Taylor is the VP of Sales and Success @ Loom, the startup that helps you get your message across by making it easy to record instantly shareable videos. To date, they have raised over $73M from some of the best in the business including Sequoia, Kleiner Perkins, General Catalyst and Point Nine to name a few. As for Sam, prior to Loom, Sam spent over 4 years at Salesforce following their acquisition of Quip, a startup Salesforce acquired for $750M where Sam was also the 1st sales leader. Before Quip, Sam spent an incredible 3 years at Dropbox where he was the first enterprise sales rep in the entire company. 

 In Today’s Episode We Discuss:

  • How Sam made his way into the world of SaaS with Dropbox and how that led to his leading the sales and success team today @ Loom?
  • What was Sam’s biggest lesson from scaling the sales team at Dropbox? How did his 4 years at Salesforce change his operating mentality? Thinking of Dropbox, how does Sam justify the role of sales in a world of product-led growth? How do product and sales work together most efficiently? What can one do to structure that relationship?       
  • Does Sam agree that the founder is the one who has to create the sales playbook? When is the right time to hire the first sales rep? Should you hire 2 at a time? What does one look for in their first sales hire? What measurements should be used to determine their success? How does this change when selling to SMBs vs enterprise?      
  • How does Sam think about the relationship between sales and marketing? Are marketing becoming the new sales team with their content being used more and more in the sales funnel? How should the success of marketing be measured? Does it have to be tied to a number related to revenue?

Sam’s 60 Second SaaStr:

  1. Biggest challenge of Sam’s role with Loom today?
  2. What would Sam most like to change in the world of SaaS?
  3. What is Sam’s biggest weakness as a sales leader? 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Dec 01, 2020
SaaStr 402: Customers Want Value + Simplicity: The Must Have's to Deliver with Marten Mickos, CEO @ HackerOne
48:33

Marten Mickos, CEO of HackerOne, explains their innovative approach of packaging customer value derived from a variety of activities into an annually recurring subscription offering that delivers outstanding value to customers while simplifying the buying process and the customer journey. 

Nov 30, 2020
SaaStr 401: The Secrets To Doing Freemium and Sales-Driven Sales at the Same Time with MixMax CEO, Olof Mathe
18:17

In this session, you will learn how to make the Freemium model work while also incorporating the traditional sales-driven strategy. Olof Mathe will share how the two strategies can blend together and specific lessons he has learned from his experience.

Nov 26, 2020
SaaStr 400: The Future of Digital Events with Ben Hindman, Co-Founder & CEO @ Splash and Jason Lemkin, CEO @ SaaStr
11:50

In today's SaaStr insider episode SaaStr CEO and Founder Jason Lemkin catches up with Ben Hindman, Co-Founder & CEO at Splash to talk about the future of digital events.

Nov 21, 2020
SaaStr 399: Four Steps to Scaling to $250M, While Keeping Community at Your Center with Prashanth Chandrasekar, CEO @ Stack Overflow
26:35

Building the world's largest and most trusted software developer and technologist community and going from 0 to 120 million users happened rapidly for Stack Overflow. Hear four steps from its CEO, Prashanth Chandrasekar, on how your product-led startup can grow its community and its revenue.

Nov 20, 2020
SaaStr 398: How To Price To Maximise For Upsell and Expansion, Why and When To Engage with Partner Programs & How To Correctly Segment Customer Profiles Most Efficiently with Rob Gonzalez, Founder & CMO @ Salsify
25:37

Rob Gonzalez is the Co-Founder & CMO @ Salsify, empowering brand manufacturers to deliver the product experiences consumers demand at every point in their buying journey. To date, Salsify has raised over $250M in funding from the likes of Venrock, Underscore, Warburg Pincus, Matrix Partners & Greenspring to name a few. As for Rob, prior to founding Salsify, he was the first-ever product manager at Cambridge Semantics and before that was a Senior Product Manager @ Endeca helping grow the company to it’s $Bn exit. 

 In Today’s Episode We Discuss:

  • How Rob made his way into the world of SaaS as a product manager and how that led to his founding Salsify over 8 years ago?
  • How does Rob think about the bundled vs unbundled thesis within SaaS? When is it right for SaaS companies to turn down potential customers? How can they do that the right way? What is the right way to think about customer segmentation? How should startups decide which customer segment to focus on?      
  • How should startups think about implementing partnerships? When is the right time? What is the right way to onboard them? How can they be trained in implementation efficiently? What does great change management look like to Rob? What does Rob believe are the biggest misconceptions around change management?       
  • How does Rob think through pricing today in a way that encourages land and expand? What can you do to make the land as frictionless as possible? What does it take to expand effectively? How does Rob think about usage vs seat-based pricing in SaaS? How should sales and marketing work together on pricing?

Rob’s 60 Second SaaStr:

  1. Most challenging element of Rob’s role with Salsify?
  2. What would Rob most like to change in the world of SaaS today?
  3. What does Rob know now that he wishes he had known at the beginning? 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Rob Gonzalez

Nov 18, 2020
SaaStr 397: Going Upmarket and How Things Have Changed in a Decade, @ Trello, with Co-Founder Michael Pryor and Jason Lemkin, CEO @ SaaStr
54:07

In today's SaaStr insider episode SaaStr CEO and Founder Jason Lemkin catches up with Michael Pryor, the Co-Founder of Trello to talk about going upmarket, and how things have changed in the last decade as Trello crosses 50M+ users. 

Nov 14, 2020
SaaStr 396: Buying patterns in the Enterprise: CEOs and More- Who's Really Buying & Why with Godard Abel, Co-founder & CEO @ G2, Mike Weir, Chief Revenue Officer @ G2 and Samantha DeStefano, Vice President, Enterprise Sales @ UpWork
23:18

As digital business and collaboration models have been permanently accelerated by the events of 2020, our panel of SaaS experts discuss who's buying in the Enterprise, and how to drive conversions across multiple business functions.

Nov 12, 2020
SaaStr 395: Why Seat Based pricing Will Die and Volume Based Pricing Is Optimal, How To Structure Pipeline Meetings Most Effectively & How To Think Through Demand Gen Strategically with UserTesting CEO Andy MacMillan
46:36

Andy MacMillan is the CEO @ UserTesting, the company that provides real-time feedback, from real customers, wherever you work. To date, they have raised over $200M in funding from the likes of Accel, Greenspring, Openview and Insight to name a few. As for Andy, prior to UserTesting, he was the Chairman and CEO @ Act On Software and before that held several positions at Salesforce, including COO - Products Group. Before Salesforce Andy spent close to 5 years at Oracle as VP Product Management. 

 In Today’s Episode We Discuss:

  • How did Andy make his way into the world of SaaS? How did he come to be CEO at the market leader, UserTesting?
  • Why does Andy think the seat-based pricing model in SaaS will die? What are the downsides of it? Why is volume-based pricing optimal? How does one instil volume based pricing without disincentivizing usage? How does Andy think about discounting? How does Andy view the importance of offering trials?       
  • What does it take to scale a sales team successfully? How can one determine a closer in the interview process? Should one hire sales reps 2x2? How does Andy think about hiring sales reps from adjacent companies and industries? How does Andy think about minimizing and optimising sales ramp times? How does Andy think about payback period?      
  • How does Andy structure the pipeline meetings? Who is invited? How are the meetings structured? How does Andy advise on the right segmentation of pipe? How does Andy evaluate the closability of the pipe? Where do many people go wrong in pipeline meetings? What have been his biggest lessons on running them successfully?

Andy’s 60 Second SaaStr:

  1. The hardest element of Andy’s role with UserTesting?
  2. What Andy would most like to change about the world of SaaS?
  3. The hardest role to hire for today and why? 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Andy MacMillan

Nov 10, 2020
SaaStr 394: How to Hack Venture Capital with Sunil Dhaliwal, GP @ Amplify Partners and and Jason Lemkin, CEO @ SaaStr
40:32

Where is Venture Capital today? And how do you hack it? SaaStr CEO and Founder, Jason Lemkin, sits down with Sunil Dhaliwal, General Partner at Amplify Partners to discuss.

Nov 06, 2020
SaaStr 393: 3 Secrets to Selling Up-Market with the Leaders of Fivetran, Stripe, and Docusign
25:29

The journey for a company to move upmarket can be daunting and varies widely depending on the internal and external factors that inspire a shift in go-to-market strategy. Join these incredible sales leaders are they share their experiences in the evolution from SMB to Enterprise.

Kelly Del Curto, Senior Director of Sales at Lever
Tammy Aguillon, Area Vice President, Commercial Sales at DocuSign
Kate Jensen, Head of Platform Sales at Stripe
Lauren Schwartz, Vice President of Enterprise Sales at Fivetran

Nov 05, 2020
SaaStr 392: 10 Simple Steps To Help Any Sales Exec Close More with SaaStr CEO and Founder Jason Lemkin
17:18

In today's SaaStr insider episode SaaStr CEO Jason Lemkin shares 10 Simple Steps To Help Any Sales Exec Close More.

Oct 30, 2020
SaaStr 391: The Secrets to Bootstrapping to $5M ARR in Less than a Year with Martha Bitar, CEO @ Flodesk
26:53

Learn how Flodesk bootstrapped to $5M in ARR by focusing on customer-driven growth: from kickstarting growth by empowering new customers to share, to creating product viral loops that amplify and optimize these customer-led funnels.

Oct 29, 2020
SaaStr 390: How To Crush It With Interactive Content, What Type, Where and When To Use It Most Efficiently and Where Many People Make Mistakes with Randy Rayess, Founder @ Outgrow
25:31

Randy Rayess is the Co-Founder @ Outgrow, a growth marketing platform that enables marketers to build interactive content/tools to increase customer engagement and boost demand generation. Prior to founding Outgrow, Randy co-founded VenturePact, an invite-only marketplace that connects companies with trusted software development firms. Before VenturePact Randy held roles at Ampush and then on the investor side at SilverLake. If that was not enough, Randy is also an investor having invested in the likes of SmartyPal, Nooch, Alie and AirCare Labs to name a few. 

 In Today’s Episode We Discuss:

  • How Randy made his way from the world of PE with SilverLake to changing the game of digital marketing with Outgrow?
  • What does interactive content mean? What are the most common forms? When should one start to use interactive content What resources and team does one need to engage with an interactive content strategy? Where do many people make mistakes with using interactive content?     
  • How should one think about idea generation for interactive content? How does one know what interactive content works best? How should we test it’s effectiveness? How should interactive content be promoted? Where should it be placed? How many text inputs is it optimal to request for?     
  • How does it convert more leads? How does Randy think about using interactive content to maximise sales rep efficiency? How should customer success engage with interactive content? What can be done to make the sales and customer success teamwork so well together?    

Randy’s 60 Second SaaStr:

  1. The hardest element of Randy’s role with Outgrow today?
  2. Hardest role to hire for today? Why?
  3. What would Randy most like to change about the world of SaaS?  

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Randy Rayess

 

Oct 28, 2020
SaaStr 389: How To Really Disrupt the Big Guys With Free with Mikael Cho, CEO @ Unsplash and Kinsey Grant, Business Editor and Podcast Host @ Morning Brew
22:21

Mikael Cho, CEO of Unsplash shares his lessons learned from starting Unsplash as a side project and growing it to a market leader, and disrupting an industry of giants like Shutterstock, Getty, and Adobe Stock with a free business model.

Oct 22, 2020
SaaStr 388: Okta CMO, Ryan Carlson on How To Measure Marketing Attribution Effectively, Why People Think About Category Creation Incorrectly Today & How You Have To Think Through The Product vs The Company Story
33:15

Ryan Carlson is the CMO @ Okta, the leading independent provider of identity for the enterprise. Prior to their incredibly successful IPO in April of 2017, they raised funding from some of the best in the business including Sequoia, a16z, Greylock, Khosla and Floodgate to name a few. As for Ryan, he has spent an incredible 9 years at Okta in numerous different roles starting with running the product marketing team before moving to run the marketing team, leading to his promotion to CMO close to 5 years ago now. Before Okta, Ryan was the Co-Founder and CEO @ Sproost, a bootstrapped online expert recommendation system. 

  In Today’s Episode We Discuss:

  • How Ryan made his way into the world of enterprise SaaS? Why was joining Okta the most challenging interview process he has experienced? How did it impact how he assesses candidates today?
  • How does Ryan distinguish between the company story vs the product story? When do they align and when do they separate? How should your strategy change as they move apart? How does the structure of your marketing team need to change with the evolution?     
  • What should the first marketing hire look like? What experience should they have? Why does Ryan believe you should hire two in marketing to start? How do you want them to work together? How does Ryan ensure cross-function working seamlessly from the very beginning with marketing?     
  • How does Ryan think about measuring success when it comes to product marketing? How does Ryan think about marketing attribution today? How should we think through SAL vs closed revenue as indicator of marketing success? Where does Ryan believe many go wrong with regards to marketing funnels?    

Ryan’s 60 Second SaaStr:

  1. What does Ryan know now that he wishes he had known at the beginning?
  2. What makes Frederic Kerrest the special leader he is?
  3. What is the most challenging element of Ryan’s role with Okta?  

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Ryan Carlson

Oct 20, 2020
SaaStr 387: Where Product Development is Going in 2021 with Nick Mehta, CEO @ Gainsight and Jason Lemkin, CEO @ SaaStr
23:47

In this CEO to CEO catch up, Nick Mehta and Jason Lemkin discuss how to do product extensions, how to sell a second product, and where product development overall is heading. 

Oct 16, 2020
SaaStr 386: How to Win When There are 1000 Players in Your Market with Adam Blitzer, EVP & GM @ Salesforce Digital Marketing Cloud
18:36

How do you compete in a tough marketplace with thousands of other competitors? Join Adam Blitzer as he shares insights from launching a company in an already crowded marketing automation space and zig-zagged the way to market leadership.

Oct 15, 2020
SaaStr 385: How To Approach Core Product Decisions in SaaS, Why Storytelling is a Lost Art in SaaS & How Product and Marketing Can Work Together Most Efficiently with Paul Rosania, Founder & CEO @ Balsa
32:39

Paul Rosania is the Founder & CEO @ Balsa, the company that recognises that builders move the world forward and so they are building the best second screen for builders, integrating tools you already use like Jira, GitHub, and Figma. Coming out of stealth today with their seed round being led by Andrew Chen @ a16z and joined by former CPO @ Slack, April Underwood, Chapter One’s Jeff Morris Jr and then of course, 20VC Fund. Prior to founding Balsa, Paul was Senior Director of Product @ Slack and before Slack was a Group Product Manager @ Twitter where he was responsible for the home timeline, including timeline ranking.

 In Today’s Episode We Discuss:

  • How Paul made his way into the world of startups with Twitter and Slack and how that led to his founding SaaS company, Balsa?
  • Paul was central in the decision-making around changing the Twitter timeline from chronological to ranked, how did he think about that decision? How does Paul approach such large product decisions today? What were his biggest operating takeaways from seeing the internal mechanics of Twitter & Slack?     
  • What does really effective product marketing mean to Paul? How does Paul think about driving really effective change management? When engaging with bottoms up sales models, where does Paul identify the tipping points of going from bottoms up to top down?     
  • Why does Paul believe that the builders are the new pro athletes? How will the structure of orgs change around them? How will the support they receive change? How will their training change? How will their comp change? How does on do this and not discourage other functions in the org?    

Paul’s 60 Second SaaStr:

  1. What does Paul believe is the hardest role to hire for today?
  2. What would Paul most like to change about the world of SaaS today?
  3. What do the next 5 years hold for Paul and for Balsa?  

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Paul Rosania

 

Oct 14, 2020
SaaStr 384: When to Launch a Second Product with Dharmesh Shah CTO and Co-Founder @ Hubspot and Jason Lemkin, CEO @ SaaStr
32:26

We caught up with one of the SaaStr community’s favorite speakers, Dharmesh Shah CTO and co-founder of Hubspot on lessons learnings launching a second product.  Hubspot recently expanded its Sales products and the learnings were top of mind.

Oct 09, 2020
SaaStr 383: Growing Product and Engineering Orgs from Zero to IPO with Nick Caldwell, VP of Engineering @ Twitter, and Tomasz Tunguz, Managing Director @ Redpoint Ventures
20:25

Nick Caldwell has built and grown product and engineering organizations at PowerBI (0 to 300 engineers), Reddit (500M MAU) and Looker ($2.7B sale to Google). Nick will share 5 big lessons he's learned along the way that you can use as you build your company's product and engineering functions from its earliest days to its largest successes.

Oct 08, 2020
SaaStr 382: What's Next For B2B and Cloud Events in 2021 with Amelia Ibarra, SVP & GM @ SaaStr, and Alon Alroy, Co-Founder & CMO @ Bizzabo
28:15

In today's SaaStr Insider, SaaStr SVP & GM, Amelia Ibarra, sits down with Alon Alroy, Co-Founder & CMO at Bizzabo on What's Next For the Future of B2B Events. 

Oct 02, 2020
SaaStr 381: Churn is dead. Long Live Net Dollar Retention Rate with Dave Kellogg, Principal @ Kellogg Consulting
21:19

There are a lot of problems with calculating churn rates. Moreover, public companies don't generally release churn rates. Learn what they are and how to calculate them correctly.

Oct 01, 2020
SaaStr 380: How To Effectively Sell Into Mid-Market, Why SEO Is The Best Kept Secret In SaaS & How To Show Credibility To Enterprise Customers as a Startup
23:03

Ryan Sandler is the Co-Founder and CEO @ Truework, the company that gives employees control over employment, income and other identity data. To date, Ryan has raised over $44M with Truework from the likes of Sequoia, Khosla, Menlo and from the founders of companies such as Plaid, Seatgeek, Mino Games and Checkr. Prior to founding Truework, Ryan spent 3 years as a Senior Product Manager @ LinkedIn.

 In Today’s Episode We Discuss:

  • How Ryan made his way from LinkedIn Product Manager to founding Sequoia backed Truework and changing the world of identity data?
  • Why does Ryan believe it is such an advantage to sell into mid-market? Where do most people go wrong here? How can startups show credibility to mid-market when they are so small? How can founders use case studies and references to build social credibility early on?     
  • What have Ryan’s lessons been when it comes to pricing? How does Ryan think about and approach discounting? How does Ryan feel about pilot plans? What elements can founders negotiate on to get the best pricing?    
  • Why does Ryan believe SEO is the best-kept secret in SaaS? How has Ryan structured his content and marketing team as a result? How can one automate as much of the content creation process as possible? How long should one expect in terms of lead times to see returns on the SEO strategy?    

Ryan’s 60 Second SaaStr:

  1. Hardest element of Ryan’s role with Truework?
  2. What would Ryan most like to change about the world of SaaS?
  3. What does Ryan know now that he wishes he had known at the beginning? 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Ryan Sandler

Sep 29, 2020
SaaStr 379: The Top 10 Mistakes Founders Make When Hiring Their First Sales Team with SaaStr CEO and Founder Jason Lemkin
16:18

From how many reps to hire, to compensation models, here are the top 10 mistakes founders make when hiring their first sales teams and how to avoid them. 

Sep 25, 2020
SaaStr 378: The 5 Things That Kill Startups After Their Seed Rounds and How to Avoid them with Michael Seibel, CEO @ Y Combinator
24:14

Investment can create more problems than it solves and founders may trick themselves into thinking they have product-market fit when they don't. Michael Seibel, CEO @ Y Combinator explores the top risks founders should be aware of after funding and his best tips to avoid them.

Sep 24, 2020
SaaStr 377: Hashicorp CEO Dave McJannet on Scaling Remote Teams; What Breaks and When, How To Successfully Execute Multi-Product Strategies and How Leadership Style Evolves with Company Stage
29:47

Dave McJannet is the CEO @ Hashicorp, one of the fastest-growing enterprise companies of our time providing consistent workflows to provision, secure, connect and run any infrastructure for any application. To date, the company has raised $349M in funding from some of the best in the business including Bessemer, Redpoint, True Ventures, IVP, Mayfield, TCV and GGV to name a few. As for David, prior to Hashicorp, he held some incredible roles including VP Marketing at Github and Hortonworks, Senior Director of Product Marketing @ VMWare and then also spent over 5 years at Microsoft. 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Sep 23, 2020
SaaStr 376: 10 Mistakes the CEO of ZoomInfo Made on His Journey to IPO with Henry Schuck, CEO @ ZoomInfo and Jason Lemkin, CEO @ SaaStr (Part 2)
34:31

In part two, ZoomInfo founder and CEO Henry Schuck shares how he built a business from scratch and grew it into one of the most successful IPOs of the 21st century—and what it was really like...the good, the bad, and most of all, the ugly. He reflects on where he went wrong, what he would do differently, and how to avoid making the same mistakes he did.

Sep 18, 2020
SaaStr 375: What Being a Founder Taught Me About Leadership - Lessons from GitHub’s COO, Erica Brescia
25:59

GitHub’s COO, Erica Brescia, shares her experiences and lessons learned from her former life on the front lines of being a co-founder of her own company, and how those lessons apply to her current position overseeing operations for GitHub. 

Sep 17, 2020
SaaStr 374: 10 Mistakes the CEO of ZoomInfo Made on His Journey to IPO with Henry Schuck, CEO @ ZoomInfo and Jason Lemkin, CEO @ SaaStr (Part 1)
30:07

ZoomInfo founder and CEO Henry Schuck shares how he built a business from scratch and grew it into one of the most successful IPOs of the 21st century—and what it was really like...the good, the bad, and most of all, the ugly. He reflects on where he went wrong, what he would do differently, and how to avoid making the same mistakes he did.

Sep 11, 2020
SaaStr 373: The State of the Cloud 2020, The COVID Beneficiaries Edition with Byron Deeter and Elliott Robinson of Bessemer Venture Partners
24:50

Bessemer's 5th Annual State of the Cloud Report returns for a definitive look at the cloud industry today. Byron Deeter and Elliott Robinson, partners at Bessemer Venture Partners, offer macro trends in the public and private cloud markets, strategic advice to cloud founders, and insights into why entrepreneurs should feel auspicious about the future.

Sep 10, 2020
SaaStr 372: Sales Kick-Off Week: How To Prepare, How To Structure, How To Organise Content, How To Keep Teams Engaged with Latane Conant, CMO @ 6Sense
27:55

Latane Conant is the Chief Marketing Officer at 6Sense, the company that allows you to achieve predictable revenue growth by identifying accounts looking for your solution, prioritise efforts and then engage the right way. To date, the company has raised $120M in financing from Battery Ventures, Insight, Venrock, Costanoa, Bain Capital and Salesforce Ventures to name a few. As for Latane, before 6Sense she was CMO and sales leader at Appirio where she drove 5X more effective field marketing programs and an increase in inbound leads by 300%. If that was not enough, Latane is also on the Advisory Boards of both Mediafly and Atrium. 

 In Today’s Episode We Discuss:

  • How did Latane make her way into the world of SaaS and come to be the rockstar CMO and ABM thought leader she is today with 6Sense?
  • What does the preparation process look like pre-sales kick off week? What is involved? Who is involved? What needs to be ready? How does Latane feel about putting comp plans as part of the week?     
  • How important is a theme to having an engaging week of content? What can teams do to bring their themes to life? How does Latane advise others when it comes to keeping the content fresh and exciting?  
  • What is the right way to end the week? What are the right follow up steps to take? Where do many people go wrong here?    

Latane’s 60 Second SaaStr:

  1. Hardest element of Latane’s role today with 6Sense?
  2. What would Latane most like to change about the world of SaaS?
  3. What does Latane believe that most around her disbelieve? 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Latane Conant

Sep 08, 2020
SaaStr 371: Learning from the Lows, How Mailchimp Navigated Economic Uncertainty with Ben Chestnut, CEO @ Mailchimp and Jason Lemkin, CEO and Founder @ SaaStr
24:26

It’s no secret that businesses today are struggling with an unpredictable economy. In this session, Mailchimp Co-founder and CEO Ben Chestnut will share the story of Mailchimp’s founding amidst—and despite—the dot-com bubble burst, and how the company navigated a number of inflection points in the first 10 years of its founding. 

Sep 04, 2020
SaaStr 370: Automation, The Digital Transformation Accelerator with Jennifer Tejada, CEO @ PagerDuty
21:07

As organizations race to achieve relevance and a competitive edge in the digital era, automation is fueling the fight. Join PagerDuty’s CEO, Jennifer Tejada, as she discusses the need for agility and innovation and how automation is aiding adaptability and allowing enterprises to surge ahead.

Sep 04, 2020
SaaStr 369: How to Hire an A-Player VP Sales and Scale Your Team with SaaStr CEO and Founder Jason Lemkin and the Co-founder and CEO of HireSweet, Robin Choy
34:29

In today’s SaaStr Insider episode, SaaStr CEO and Founder Jason Lemkin and the Co-founder and CEO of HireSweet, Robin Choy, share their experiences building and scaling their companies.

Today's SaaStr insider originally aired on A-Players, a new podcast that teaches you how to hire, retain, and train top performers for your team! 

Aug 28, 2020
SaaStr 368: 5 Insights for Consumerization of the Enterprise with Scott Belsky, CPO and EVP @ Adobe Creative Cloud
25:46

Success in the Enterprise means ensuring consumerization is a part of your strategy. Scott Belsky, CPO, EVP of Creative Cloud at Adobe will explore key tactics to focus on the user experience.

Aug 27, 2020
SaaStr 367: Zoom's Head of Global Sales Operations on Sales Ops vs Revenue Ops, The Biggest Areas of Operational and Strategic Debt for Sales Teams Today & The Importance of Documentation and The Dangers of Dirty Data
34:59

Hilary Headlee is Head of Global Sales Operations and Enablement @ Zoom. Prior to joining Zoom, Hilary was VP of Global Sales Operations and Productivity @ MindBody and before that enjoyed similar roles with Alteryx, Invoca and Lynda.com. At Lynda.com, Hilary grew the support teams from 6 to 60 people and supported more than 60 net new reps in just 3 years. If that was not enough, Hilary is also a Limited Partner in Stage 2 Capital, the venture firm focused purely on go-to-market. 

 In Today’s Episode We Discuss:

  • How did Hilary make her way into the world of SaaS and come to be the sales leader she is today with the global communications leader, Zoom?
  • When thinking about sales ops vs revenue ops, what are the 4 key points to consider for founders? How does lead management and onboarding alter the question of sales ops vs revenue ops? Where does Hilary see operational debt the most? How does she advise founders on removing it?    
  • Given the broad scope of sales ops and engagement, is it not just rebalancing culture, comms and change? As a business scales does there not come a time where it unbundles and scales out of sales vs revenue ops? How do the roles change with time and scale? Where do the breakpoints occur? 
  • Why does Hilary believe documentation is so important today? What is the toolset Hilary uses for documentation? How does Hilary train her team around the right strategy to document their processes? Where do many go wrong here? Where can you pick up small wins?   

Hilary’s 60 Second SaaStr:

  1. What is the hardest element of Hilary’s role today with Zoom?
  2. What would Hilary most like to change in the world of SaaS today? 
  3. What does Hilary believe that most around him disbelieve? 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Aug 26, 2020
SaaStr 366: Digital Transformation At Warp Speed with Jason Lemkin, CEO and Founder @ SaaStr, and Aaron Levie, CEO, Co-founder and Chairman @ Box
52:06

The buzz that accompanies digital transformation trends is infinite. Cut through the noise with Aaron Levie, CEO of Box and Jason Lemkin, CEO & Co-founder of SaaStr as they share insights on what will make a lasting impact and what may fail to materialize in the future of work.

Aug 21, 2020
SaaStr 365: The Office of the Future, How Everything's Changed and What 2021 Will be Like with Justin Bedecarre, CEO @ HelloOffice and Jen Nguyen, Founding Partner @ TEAMWERC
21:21

Centralized HQs with all the perks and amenities “under one roof” have traditionally been used as recruiting tools to attract and retain top talent. In this episode, Justin and Jen discuss what the Office of the Future will be like. 

Aug 20, 2020
SaaStr 364: Figma's Head of Sales, Kyle Parrish on Why Scaling From 0-1 In Sales Is So Damn Hard, The Biggest Lesson From Moving Sales Outside Core HQ & How To Create A Performance Led Culture
38:22

Kyle Parrish is the Head of Sales @ Figma, the company that helps teams create, test and ship better designs from start to finish. To date the company has raised over $132M in financing from some of the best in the business including Sequoia, a16z, Index, Greylock and Kleiner Perkins to name a few. As for Kyle, prior to Figma he spent over 5 years at Dropbox achieving some incredible milestones including launching and scaling the Austin, Texas office from 3 to 80 people and being responsible for growing Dropbox’s leading partner ecosystem. Before Figma, Kyle spent close to 3 years as an Account Executive at ADP. 

 In Today’s Episode We Discuss:

  • How Kyle made his way into the world of SaaS and sales and came to be Head of Sales at one of the fastest-growing companies in Figma?
  • Kyle was in charge of creating the Austin, Texas sales team @ Dropbox, what were some of his biggest lessons when it comes to moving sales outside of HQ? What worked? What did not work? At what stage does culture and process really start to break?    
  • Why is it so hard moving from 0-1 in sales? How does Kyle advise founders when it comes to making your first sales hire? Does Kyle agree that it has to be the founder who develops the sales playbook? How does one create sales targets that are both ambitious but also achievable? What is the balance? 
  • What does it take to create a performance led sales culture? Where do many people go wrong here? How is the best way for sales and product to work together? What can one do to proactively make those discussions with sales and product both frequent and productive?   

Kyle’s 60 Second SaaStr:

  1. What is the hardest element of Kyle’s role today with Figma?
  2. What would Kyle most like to change in the world of SaaS today? 
  3. What does Kyle believe that most around him disbelieve? 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Kyle Parrish

The future of work is here and digital automation is now essential for today’s workforce. Tools have improved, but companies are STILL using outdated and manual processes to conduct business. Enter Pipefy. Pipefy is a workflow management software that makes business processes such as purchasing, onboarding, and recruiting—hassle-free, so requesters, processors and managers are more efficient. Pipefy seamlessly integrates with other tools in your toolchain to ensure a completely automated experience with a low to no code implementation. Dispersed or remote team members? NO PROBLEM! Pipefy can automate your requests from anywhere. Scroll over to pipefy.com/saastr to try it out and get 10% off your first 3 months. Empower your teams everywhere with Pipefy.

Aug 18, 2020
SaaStr 363: How to Make 1,000,000 Customers Happy with Jason Lemkin, CEO and Founder @ SaaStr, and Loren Padelford, General Manager @ Shopify Plus
49:06

Small, Medium, or Enterprise, SaaStr CEO Jason Lemkin sits down with Shopify Plus GM, Loren Padelford, to discuss how to keep your customers happy at all stages.

Aug 14, 2020
SaaStr 362: The Future of the Customer with Bernadette Nixon, CEO @ Algolia, Jay Snyder, Chief Customer Officer @ New Relic, and Nick Mehta, CEO @ Gainsight
24:59

Customers' expectations are higher than ever with more access to information and options. This dynamic trio of SaaS experts share how to stay customer-centric and set yourself apart in today's rapidly changing environment.

Aug 13, 2020
SaaStr 361: The 4 Phases of Company Growth & What Breaks At Each Stage, How To Instill Process with Scale Without Adding Barriers and What Great Change Management in a COVID World Looks Like with Lara Caimi, Chief Customer and Partner Officer @ ServiceNow
31:47

Lara Caimi is the Chief Customer and Partner Officer @ ServiceNow, the company that allows you the power to make work, work better. Prior to their IPO, ServiceNow raised funding from some of the best in the business including Sequoia Capital and Greylock. As for Lara, she joined ServiceNow in 2017 and spent 3 years as Chief Strategy Officer before assuming her current role just this month. Before ServiceNow Lara spent an incredible 17 years at Bain & Co across a variety of different projects and roles.

 In Today’s Episode We Discuss:

  • How Lara made her way into the world of ServiceNow and SaaS having spent an incredible 17 years at Bain & Co?
  • What does the role of Chief Strategy Officer really entail? How did the role change in Lara’s 3 years in the position? What is the optimal relationship between the Chief Strategy Officer and the CEO? How does Lara advise founders on when to hire their Chief Customer Officer?  
  • How does Lara see the 4 phases of startup growth? What are the most challenging elements within each? How does one instil process and discipline without losing agility and speed? How does one set targets that are a stretch but also not a stretch too far? What is the right balance? 
  • How does Lara think about what great change management looks like today? How does that change in a COVID world? How does Lara approach the right way to address enterprise customer communications? Why has that been made easier in COVID times?  

Lara’s 60 Second SaaStr:

  1. What would Lara most like to change in the world of SaaS today?
  2. What is the hardest element of Lara’s role with ServiceNow today?
  3. The biggest surprise for Lara internally since the start of COVID? 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

The future of work is here and digital automation is now essential for today’s workforce. Tools have improved, but companies are STILL using outdated and manual processes to conduct business. Enter Pipefy. Pipefy is a workflow management software that makes business processes such as purchasing, onboarding, and recruiting—hassle-free, so requesters, processors and managers are more efficient. Pipefy seamlessly integrates with other tools in your toolchain to ensure a completely automated experience with a low to no code implementation. Dispersed or remote team members? NO PROBLEM! Pipefy can automate your requests from anywhere. Scroll over to pipefy.com/saastr to try it out and get 10% off your first 3 months. Empower your teams everywhere with Pipefy.

Aug 10, 2020
SaaStr 360: What’s Changed Since March 15 The Cloud at Hyperspeed. The World in Flux with Jason Lemkin, CEO and Founder of SaaStr, and Rob Bernshteyn, CEO and Founder of Coupa
51:53

Digital transformation marks a radical rethinking of how companies use tech, people, and operations to fundamentally change their business performance. Coupa CEO, Rob Bernshteyn, and SaaStr CEO, Jason Lemkin, will discuss how the Cloud has changed in 2020.

Aug 07, 2020
SaaStr 359: The Secrets to Vertical Growth, What it Really Takes to Build a $1B SaaS Company with Matt Garratt, SVP, Managing Partner @ Salesforce Ventures, Trisha Price, Chief Product Officer @ nCino and David Schmaier, CEO & Founder @ Vlocity
23:53

From strategies in recruitment and team building to sales tactics, these leaders from Salesforce, nCino, and Vlocity, will discuss the top tips for moving beyond horizontal SaaS and building a billion-dollar SaaS company.

Aug 06, 2020
SaaStr 358: Why Ignoring Customer Feedback Can Be Critical To Success, Why Founders Need To Change The Way They Think About LTV and How To Create a Pricing Model That Aligns Your Success To Your Customer's with Chen Amit, Founder & CEO @ Tipalti
36:09

Chen Amit is the Founder & CEO @ Tipalti, the only global payable automation platform that scales with you and now remitting $5Bn annually across 3M suppliers. To date, Chen has raised over $146M with Tipalti from the likes of Oren Zeev, Dan Rose, Mike Chalfen and then Greenspring, Truebridge and 01 Advisors to name a few. Previously, Chen was CEO of Atrica, acquired by Nokia-Siemens. He also was co-founder and CEO of Verix. At ECI Telecom, Chen founded its ADSL business unit and led it from inception to $100 million in annual sales. 

 In Today’s Episode We Discuss:

  • How Chen made his way into the world of SaaS and came to found the leader in account payables with Tipalti?
  • Why does Chen believe so much of his success is derived from saying no to customers? How does Chen determine which customer feedback to ingest vs to reject? If rejected, how can startups do this in a polite and respectful way? How can startups give the appearance of a large company to enterprises?   
  • Given the infinite supply of capital, how does Chen think about unit economics? How does Chen think the right way to calculate LTV is? Where do many go wrong? What can we learn from Amazon when it comes to LTV? How does Chen advise founders to think about annual dollar churn? 
  • How does Chen think about optimising pricing models today? How can SaaS companies have variable pricing mechanisms without disincentivizing usage? How does Chen think about aligning revenue scale to your customers? How can this be done? What are the benefits?  

Chen’s 60 Second SaaStr:

  1. What is the hardest element of Chen’s role today with Tipalti?
  2. What would Chen most like to change in the world of SaaS today? 
  3. What does Chen believe that most around him disbelieve? 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

The future of work is here and digital automation is now essential for today’s workforce. Tools have improved, but companies are STILL using outdated and manual processes to conduct business. Enter Pipefy. Pipefy is a workflow management software that makes business processes such as purchasing, onboarding, and recruiting—hassle-free, so requesters, processors and managers are more efficient. Pipefy seamlessly integrates with other tools in your toolchain to ensure a completely automated experience with a low to no code implementation. Dispersed or remote team members? NO PROBLEM! Pipefy can automate your requests from anywhere. Scroll over to pipefy.com/saastr to try it out and get 10% off your first 3 months. Empower your teams everywhere with Pipefy.

Aug 03, 2020
SaaStr 357: Busting the Myths About Startup Success with Therese Tucker, CEO and Founder of BlackLine
21:32

Therese Tucker breaks through the dogma behind what it takes to build a successful tech company. With stories based on the founding of BlackLine — to the company’s successful IPO – you’ll learn the most common myths behind success and why they may be holding you back.

Jul 30, 2020
SaaStr 356: When To Hire Your First Sales Reps, What To Look For In Those Hires, What Good Sales Rep Onboarding Looks Like, Leading Indicators of Sales Rep Success and more with Pete Kazanjy, Co-Founder @ Atrium
41:36

Pete Kazanjy is the Co-Founder @ Atrium, the startup providing proactive, always-on insights for sales operations, managers, and leaders. Stop asking questions. Start getting answers. Alongside Atrium, Pete is also the Founder of Modern Sales Pros, a community of 15,000 focused on sales operations and sales management. Pete is also the author of Founding Sales, the canonical writing on early-stage startup sales. Prior to founding Atrium, Pete founded TalentBin, culminating in their exit to Monster Worldwide in February 2014. Finally, before TalentBin, Pete founded Honestly.com building the world's first professional reputation clearinghouse and raising funding from CRV and First Round in the process. 

 In Today’s Episode We Discuss:

  • How Pete made his way into the world of SaaS and how he came to be one of the leading figures on sales operations and management that he is today?
  • Why do founders have to sell the product themselves at the start? When is the right time to hire their first sales reps? What profiles should founders look for in these first reps? What are the most common mistakes founders make when hiring their first reps? How should they structure their comp plans?   
  • How do the best onboard their sales reps? What can be done to minimise ramp time of new reps? How is the documentation used most effectively? How can sales calls be used for new rep onboarding? How does Pete think about optimising payback period on a per rep basis? 
  • What are the leading indicators that a sales rep is successful? What are the core metrics founders should measure to determine the effectiveness of their reps and sales teams? How does this differ between SMB and enterprise? What are the challenges with enterprise given the long sales cycles? 

Pete’s 60 Second SaaStr:

  1. Hardest element of Pete’s role today with Atrium?
  2. What would Pete most like to change in the world of SaaS?
  3. What sales leader does Pete most respect and why?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Pete Kazanjy

Jul 28, 2020
SaaStr 355: The PPP You Really Need for Raising Capital During a Pandemic with Satya Patel, Partner at Homebrew
21:50

Despite the global pandemic, seed investing remains hyperactive amongst VCs. Satya Patel of Homebrew shares his expert advice on how to raise seed capital in 2020. 

Jul 23, 2020
SaaStr 354: 10 Things I Wish My Board and Investors Had Told Me with Jason Lemkin, CEO, and Founder of SaaStr
19:28

Whether you've just raised your first round or are in hypergrowth mode, here are the 10 things SaaStr CEO and Founder, Jason Lemkin, wishes his board and investors had told him. 

Jul 17, 2020
SaaStr 353: Unicorns and Decacorns in 2020: What's Changed and What Hasn't with Keith Rabois, General Partner at Founders Fund and Jason Lemkin, CEO, and Founder of SaaStr
28:04

Keith Rabois (Paypal, Linkedin, Square) and SaaStr Founder Jason Lemkin talk about the landscape of SaaS & Cloud fundraising and valuation in 2020. 

Jul 16, 2020
SaaStr 352: SaaS Decacorns and The Covid Beneficiaries with SaaStr CEO and Founder Jason Lemkin
14:22

Decacorns ($10B+ valuation) are everywhere in SaaS, despite the downturn.  SaaStr CEO Jason Lemkin discusses what the new landscape of SaaS means for you in 2020. 

Jul 10, 2020
SaaStr 351: How to Adjust your Sails to Navigate Today’s Choppy Waters with Chris O'Neill, Partner at Portag3 Ventures
23:15

Chris O'Neill (Google, Evernote) shares his lessons from previous downturns and how to chart a new course for growth in today's changing market.

Jul 09, 2020
SaaStr 350: Scaling SaaS To Well Over $1M ARR with No Funding, How Being A Sommelier Helped Neha Break The Glass Ceiling of Business & How to Successfully Scale Remote Teams Efficiently
35:49

Neha Sampat is the Founder and CEO @ Contentstack, a modern content management system bringing business and tech teams together to deliver personalised, omnichannel experiences. Atypical in our world, but Neha scaled the business to well over $1M in ARR before raising funding. Now Neha has raised over $31M from the likes of Insight Partners and Illuminate. Prior to Contentstack, Neha was the Founder and CEO @ Built.io and before that spent 10 years as the Founder and CEO @ Raw Engineering, building a leading digital transformation consultancy.

 In Today’s Episode We Discuss:

  • How did Neha make her way into the world of SaaS and content management systems having previously built a digital transformation agency?
  • How the heck did Neha scaled Contentstack to over $1M in ARR without raising capital, whilst being based in the Bay? What were the signals that made Neha realise she had a scalable software business? What did Neha look for in her first seed round investors? How did that profile change when she went out to raise the Series A?  
  • How has being a sommelier helped Neha break the glass ceiling of business? What are some lessons Neha has learned in terms of build true and genuine relationships with customers beyond the transaction? What are the counter-intuitive strategies Neha has found works when it comes to motivating remote teams?
  • Why did Neha decide to build out so much of the tech team well outside of the Bay in a town outside of Mumbai? Does Neha believe the future of tech is in the valley or decentralised?  

Neha’s 60 Second SaaStr:

  1. Neha’s biggest strength and biggest weakness as a leader?
  2. What does Neha believe that many around her do not?
  3. The biggest obstacle to the success Neha has achieved?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Neha Sampat

Jul 06, 2020
SaaStr 349: How to Turn Your SaaS Startup Into an Army with David Sacks, General Partner at Craft Ventures
28:36

Startups can get messy. Especially in growth. David Sacks (Yammer, PayPal) shares how to navigate from 50-500 employees.

Jul 02, 2020
SaaStr 348: How To Align Your Pricing To The Success of Your Customers, What Does Great Change Management Look Like and The Right Balance Between Software vs Services Revenue with Kurt Muehmel, Chief Customer Officer @ Dataiku
31:34

Kurt Muehmel is the Chief Customer Officer @ Dataiku, the platform democratizing access to data and enabling enterprises to build their own path to AI in a human-centric way. To date, the company has raised over $146M in funding from some of the best in the business including ICONIQ, Firstmark, Battery Ventures and CapitalG to name a few. As for Kurt, he joined the company over 5 years ago and has risen from AE to VP EMEA to VP Sales Engineering to today as Chief Customer Officer. Before Dataiku, Kurt spent 5 years at Deloitte as a Manager advising primarily European public authorities on sustainable development policies.

 In Today’s Episode We Discuss:

  • How Kurt made his way into the world of enterprise SaaS with Dataiku having started his career at Deloitte in Paris?
  • What does it take to go from 0-1 in implementing both AI and data science disciplines in 20th-century companies? Where do many go wrong with their first steps? How can one assist them in the right way? How does Kurt feel about services revenue? At what stage or ratio does it become too much? 
  • How does Kurt approach the challenge of change management? What does great change management look like? Where do so many go wrong? How can content be used to efficiently scale change management practices? How does one need to engage different teams for effective change management? 
  • How does Kurt think about the right pricing mechanism for the customer today? How does one find a mechanism that does not disincentivize the customer with usage? How does Kurt feel about discounting? To what extent is Kurt and Dataiku willing to engage with pilots and POCs? Where do many go wrong here? 

Kurt’s 60 Second SaaStr:

  1. Biggest challenge of Kurt’s role with Dataiku today?
  2. What does Kurt know now that he wishes he had known when he entered the world of SaaS?
  3. Who does Kurt look up to in the world of customer experience? Why?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Kurt Muehmel

Jul 01, 2020
SaaStr 347: Top 10 Questions to Ask a VP of Sales with SaaStr CEO and Founder, Jason Lemkin
17:38

Ready to hire your first VP Sales?  But haven’t done it before? SaaStr CEO, Jason Lemkin shares his interview checklist. 

Jun 26, 2020
SaaStr 346: What Nobody Tells You About Seed Investing, The Inside Scoop with Aileen Lee of Cowboy Ventures and Jason Lemkin of SaaStr
19:25

Aileen Lee is a U.S. seed investor. A venture capital investor, she is the founder of Cowboy Ventures. Lee coined the often-used Silicon Valley term unicorn in a TechCrunch article "Welcome To The Unicorn Club: Learning from Billion-Dollar Startups."

In this episode of the SaaStr podcast, Aileen and SaaStr Founder Jason Lemkin take a deep dive on how Aileen finds deals, her tips for a winning pitch, and the state of VC in 2020. 

Jun 25, 2020
SaaStr 345: PagerDuty CMO Julie Herendeen on Attribution and Accountability within Marketing Teams, The Optimal Relationship Between Marketing & Product & Why Customer Success and Marketing Have Never Been Closer
33:15

Julie Herendeen is the CMO @ PagerDuty, the real-time operations platform ensuring less downtime and fewer outages, meaning happier customers and more productive teams. Prior to their IPO in 2019 PagerDuty raised funding from some of the best in the business including Accel, a16z, Baseline, Bessemer and Harrison Metal to name a few. As for Julie, prior to PagerDuty she was Vice President of Global Marketing @ Dropbox. Before Dropbox Julie was CMO @ Lookout and before Lookout, Julie enjoyed VP roles at both Yahoo and Shutterfly. If that was not enough, alongside her role at PagerDuty today Julie is also an angel with Broadway Angels and a Board Member @ Hubspot. 

 In Today’s Episode We Discuss:

  • How Julie made her way from the world of consumer into the world of enterprise and came to be CMO @ PagerDuty today? What were some of Julie’s biggest lessons from her time as VP Global Marketing at Dropbox?
  • Does Julie believe that marketing should be held accountable to a number tied directly to revenue? How does Julie believe sales and marketing should work in unison? How can sales be involved in pipeline generation meetings? Should AEs make themselves responsible for sourcing new leads also? What does the ideal handoff look like? 
  • How does Julie see the best marketing and product teams working together? What can marketing do to collect the most valuable data to inform product decisions? In what forum should they be relayed to product teams? How should product and marketing leaders interact most efficiently? 
  • How does Julie think about the relationship of customer success and marketing? Does Julie agree that with the increasing amount of marketing content used post-sale, marketing is doing much of the work of CS? Where does Julie see many going wrong when investing heavily into thought leadership and content marketing?

Julie’s 60 Second SaaStr:

  1. Which marketing leader does Julie most respect and why?
  2. What would Julie most like to change about the world of SaaS today?
  3. What is the optimal relationship between the CEO and the CMO?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Julie Herendeen

Jun 23, 2020
SaaStr 344: 16 Mistakes Founders Make Pitching to VCs with SaaStr CEO and Founder, Jason Lemkin
22:49

Given that so many VC pitches are over Zoom now, we thought it would be worth sharing the things it’s easy to get wrong when pitching investors.

Pitching VCs is like anything.  You’ll get better at it over time.  Later, you’ll even get great at it.  Once you know how it works, it’s not even that hard to knock it out of the park.

But until then, so many founders make unforced errors.   Rookie errors.  Here are 16 that you can easily avoid / fix right now today.

Jun 19, 2020
SaaStr 343: Point Nine Capital Managing Partner, Christoph Janz, On Fundraising During a Pandemic
19:00

On today's episode, Christoph shares his five tips for fundraising during a pandemic. 

  1. Have a clear COVID-19 assessment 
  2. Start with an extra-long "long list"
  3. Disqualify ruthlessly
  4. Have a killer deck 
  5. Build trust remotely 

Christoph has invested in more than 20 SaaS startups and lives and breathes SaaS, everything from “A as in AI-enhanced B2B software” to “Z as in Zendesk”. Christoph co-founded Point Nine Capital in 2011.

Before that, he co-founded two Internet startups (DealPilot.com in 1997 and Pageflakes in 2005). In 2008 he became an angel investor and discovered Zendesk, Clio, FreeAgent – and his love for SaaS.

Jun 18, 2020
SaaStr 342: Zapier CEO, Wade Foster, and SaaStr CEO, Jason Lemkin, on Distributed Teams and Building a Cloud Product
25:28

On this episode of the SaaStr podcast, our CEO, Jason Lemkin, chats with Zapier CEO, Wade Foster, on Distributed Teams and Building a Cloud Product.

Zapier is a global remote company that allows end-users to integrate the web applications they use. Although Zapier is based in Sunnyvale, California, it employs a workforce of 250 employees located around the United States and in 23 other countries.

Jun 11, 2020
SaaStr 341: Leading Indicators Individuals Can/Can Not Scale with the Company, What Radical Transparency Truly Means and How To Implement It & Enterprise Adoption Of Cloud During COVID Times with David Politis, Founder & CEO @ BetterCloud
33:44

David Politis is the Founder & CEO @ BetterCloud, the company that helps IT discover, manage and secure the digital workplace. To date, David has raised over $186M in funding with BetterCloud from the likes of Accel, Warburg Pincus, Greycroft, Flybridge and Dropbox to name a few. Before founding BetterCloud, David was an early employee of Cloud Sherpas (acquired by Accenture), where he led the company to become the leading cloud services partner to SMB worldwide. Prior to Cloud Sherpas, David was a founding employee and General Manager of Vocalocity (acquired by Vonage), which he grew into one of the top providers of cloud PBX technology.

 In Today’s Episode We Discuss:

  • How David made his way into the world of SaaS and came to found BetterCloud? How has David seen the rate of cloud adoption within enterprise over the last 5 years? Has it been faster or slower than he thought? 
  • People often suggest operators are suited to certain stages of a company lifecycle, does David agree with this? What are the leading indicators an individual is struggling to scale? How does one communicate that to them effectively? How does David think about the decision to move an individual to another role vs release them? 
  • What does radical transparency really mean to David? How does the ability to have radical transparency within your org change when the org is 10 people vs 100 people? What are the biggest challenges of scaling transparency? From a meeting structure view, what can leaders do to encourage transparency? 
  • How does David feel about the method of OKR setting? How has his mindset changed towards OKRs? What does the decision-making process look like for deciding which OKRs to focus on? What OKRs do they focus on at BetterCloud? How does one know when they need to change their OKRs?

David’s 60 Second SaaStr:

  1. What would David most like to change in the world of SaaS?
  2. How has David seen himself emerge and develop as a leader?
  3. What is the biggest challenge of David’s role within BetterCloud today?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

David Politis

Jun 09, 2020
SaaStr 340: Mark Suster, Managing Partner at Upfront Ventures, on Funding In the Time of Coronavirus
29:04

Mark Suster is a managing partner at Upfront Ventures, the largest venture capital firm in Los Angeles, and a prominent blogger in the startup venture capital world.

In this episode of the SaaStr podcast, he shares his learnings on the current landscape of funding in the time of Coronavirus, including:

  • Valuation and compression 
  • Forecasting market trends
  • The slowdown in VC
  • His best advice for surviving the downturn and raising a round of funding 
Jun 04, 2020
SaaStr 339: Why SaaS Playbooks Are For Suckers, How To Make Sales Data Truly Actionable & The Right Way To Run Sales Meetings with Michael Katz, Founder & CEO @ mParticle
29:42

Michael Katz is the Founder & CEO @ mParticle, the customer data platform for brands leading the customer data revolution with clients from Airbnb to Spotify to Postmates. To date Michael has raised over $120m in funding with mParticle from GV, Social Capital, Greylock, Bain Capital Ventures and a friend of the show in Zach Coelius. Prior to founding mParticle, Mike was the Founder & CEO @ Interclick, where he organically grew revenue to over $140m in 5 years. The company went public in 2009 and was acquired by Yahoo in 2012 for $270m, a 50% premium on existing share price. If that was not enough, Michael is also on the board of Brightline and a mentor with Techstars.

 In Today’s Episode We Discuss:

  • How Michael made his way into the world of SaaS and enterprise SaaS having founded and IPO’d an adtech business previously?
  • Why did Michael make the move to CRO 8 months ago? How does Mike think about when is the right time to hire your first CRO? How does this hire correlate to your hiring in sales enablement? What are the different CRO profiles Mike has seen? How does Mike advise founders on those that work best for early-stage?
  • Why does Mike believe that playbooks are for suckers? What is the reasoning for the reductionism towards the power of the playbook? How does Mike think about the relationship between playbooks and predictability? 
  • How does Mike make sales data really actionable within the company? What is the right way for founders to do post-mortems on won and lost deals? What is the right way to structure their sales pipeline? Who should be involved in analysing this data? What can be done to incentivize sales to be accurate in their sales data?
  • Why does Michael believe that most sales meetings are unproductive? What is the right way to structure your sales meeting? Who should be brought into the meeting other than the sales team? How does Michael advise sales reps to maintain customer relationships post-sale? Where do many go wrong here? 

Michael’s 60 Second SaaStr:

  1. What would Michael most like to change about the world of SaaS?
  2. What is the hardest element of Michael’s role today with mParticle?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Michael Katz

Jun 02, 2020
SaaStr 338: Slack CEO Stewart Butterfield on Taking Care of Your Team and Your Customers
25:17

These are unique times. In some ways, we can use our playbooks, make adjustments, and in other ways, things are very different. What isn’t likely to be very different is that recurring revenue … recurs. This is the bedrock of SaaS.

Hear how Slack CEO, Stewart Butterfield, is adapting to change and his advice on how to take care of your team and customers. 

May 28, 2020
SaaStr 337: Scaling A SaaS Business Within A Non-SaaS Business, What CIOs Want To See In Pricing Models and What Great Change Management Looks Like with Head of America's for Facebook's Workplace, Christine Trodella
25:04

Christine Trodella is Head of Americas for Facebook’s Workplace product, the communication tool that connects everyone in your company, through Groups, Chat, Rooms and Live video broadcasting. Prior to Workplace, Christine was Head of America’s for Facebook’s Audience Network and before that spent 5 years as a Group Director across multiple different sales and account teams within Facebook’s mid-market channel. Before Facebook, Christine was an Executive Director @ WebMD and before that spent close to 3 years in media sales at Yahoo. 

 In Today’s Episode We Discuss:

  • How Christine made her way into the world of SaaS as part of a non-SaaS company and how that led to her leading Americas for Workplace by Facebook?
  • What have been the biggest benefits of scaling a SaaS company within a non-SaaS company? What are the biggest challenges or misalignments of scaling Workplace within Facebook? What have been some of the core and early mistakes the team made in their strategy to build out the Workplace sales and marketing machine? 
  • What have been Christine’s biggest lessons on what it takes to sell really effectively to some of the largest enterprises in the world? What do CIOs most want in pricing? How does Christine think about the pricing problem of having a variable pricing mechanism without disincentivizing usage? How does Christine think about and approach discounting?
  • Does Christine believe remote is the new normal? What really interesting data have Christine and the Workplace team seen since the world has move to work from home? How has behaviour changed on the platform with the rise of remote work? 

Christine’s 60 Second SaaStr:

  1. What would Christine most like to change in the world of SaaS?
  2. When I say success, who is the first person that comes to Christine’s mind?
  3. What is the biggest challenge of Christine’s role within FB today?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Christine Trodella

Lower your burn by leveraging AI to claim R&D tax credits for a flat fee. Cash on hand is more important than ever, CrossBorder Solutions helps you keep more of your money. See why AI is the rational choice, request a demo today. [crossborder.ai/20]

May 26, 2020
SaaStr 336: Salesforce Ventures Managing Partner Matthew Garratt and Salesforce SVP of Commercial Sales, Adnan Chaudhry on Shifting Your Sales & GTM Strategy in Uncertain Times
24:22

Leveraging survey data from 66+ enterprise SaaS companies, Matt Garratt, Managing Partner of Salesforce Ventures shares the landscape of how businesses are shifting their sales & GTM strategies to react to today's uncertain times. Adnan Chaudhry, SVP of Sales at Salesforce then provides actionable takeaways on how to refocus your sales teams, engage with customers, adjust your sales comp and how you can properly forecast in today's new landscape.

May 21, 2020
SaaStr 335: How To Plan, Organise and Execute A World Class Virtual Event in a COVID World with David Spinks, Founder @ CMX Media
35:36

David Spinks is the Founder @ CMX, the premier network for community professionals. In 2019, CMX was acquired by Bevy, where David now serves as the VP of Community. Bevy is a customer-to-customer community management platform, building products that brands use to build, grow and manage their community event programs, both virtual and IRL for companies like Slack, Twitch, Salesforce, Atlassian, and Duolingo. Prior to CMX, David founded 2 prior startups centred around different forms of community building and before that was Community Manager in the early days of LeWeb the largest tech/startup conference in Europe.

 In Today’s Episode We Discuss:

  • How David made his way into the world of SaaS and came to found CMX? Why David believes that community is so central for all SaaS companies today?
  • How does David advise teams on expectation setting around virtual events? How ambitious should they be? What big mistakes does David often see in the early days of the planning? How does this differ if you have an existing cohort of users vs are starting new with no audience?  
  • How dependent is the success of the community on the platform it is hosted on? What is the ideal size for Slack, Telegram and Whatsapp communities? Should the host seed the discussion or allow it to be natural? How important is it to establish a handbook of expected actions and behaviours? Should you cull members who are inactive? 
  • What does David believe separates good from great when it comes to discussion groups? What innovative strategies has David seen work when it comes to bringing a virtual event to life? What is the right amount of people in that discussion group? What is the core role of the moderator for the group?

David’s 60 Second SaaStr:

  1. Biggest misconception around virtual events?
  2. Virtual events: Permanent tide change or purely in the COVID world?
  3. What has been David’s favourite virtual event? Why?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

David Spinks

Lower your burn by leveraging AI to claim R&D tax credits for a flat fee. Cash on hand is more important than ever, CrossBorder Solutions helps you keep more of your money. See why AI is the rational choice, request a demo today. [crossborder.ai/20]

May 19, 2020
SaaStr 334: Cloudflare COO Michelle Zatlyn on The Top 10 Lessons Learned Starting Something Big During Tough Times
21:45

Hear from Michelle Zatlyn, co-founder and COO of Cloudflare. Michelle started the company during an economic downturn in 2009. Now, Cloudflare runs one of the world's largest networks that helps make the Internet more secure, fast, and reliable, with a market cap of more than $6B. Despite the challenges of uncertainty, money not flowing, and a generally dark mood, she was able to do it and learned a lot along the way. In this talk, Michelle will share how she made her business idea come to life and some lessons learned that can help other entrepreneurs—from solving a real, meaningful problem, to communicating in a crisis, prioritizing when there's a true lack of resources, and more.

May 14, 2020
SaaStr 333: How To Create and Structure Your Customer Success Strategy, How Customer Success Teams Can Build Relationships of Trust with Customers and How Maslow's Hierarchy of Needs Drives Customer Success Roadmaps with Bridget Gleason, Head of Sales & C
37:32

Bridget Gleason is the Head of Sales and Customer Success @ Tidelift, the company providing managed open source, backed by maintainers. Tidelift has raised over $40M from some of the best in the business including Foundry Group and General Catalyst. As for Bridget, she has the most incredible track record. Before Tidelift, Bridget was VP of Sales @ Logz.io and before that was VP of Corporate Sales @ Sumo Logic where she drove ARR up by a record 237%. Prior to SumoLogic, Bridget was VP of Sales @ YesWare where she increased MRR per rep by 450%. Finally, before YesWare, she was VP of Sales @ Engine Yard, where she tripled monthly recurring revenue, over the course of her 3+ year tenure, in 3 key leadership roles.

 In Today’s Episode We Discuss:

  • How Bridget made her way into the world of SaaS and Sales and came to be Head of both Sales and Customer Success at Tidelift?
  • Why does Bridget believe the best starting point for customer success is “company culture and value”? How does company culture impact the quality of customer success? In practice, what can one do to improve it? Who has done this well? How does value drive customer success forward? 
  • How does Bridget think Maslow's Hierarchy of Needs drives the roadmap for customer success? What core elements does it change? Where do most teams go wrong in implementing the role out of their CS strategy? When should one hire their first CS rep? What should that hire look like from an experience perspective?
  • How does Bridget advise her CS reps the best ways for them to build trust with their clients? What works? What does not work? Does Bridget believe CS teams should be involved in the upsell process? Does that endanger the element of trust?

Bridget’s 60 Second SaaStr:

  1. What does Bridget know now that she wishes she had known when she entered the world of SaaS?
  2. What would bridget most like to change about the world of SaaS today?
  3. What is the most challenging element of Bridget’s role with Tidelift?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Bridget Gleason

Lower your burn by leveraging AI to claim R&D tax credits for a flat fee. Cash on hand is more important than ever, CrossBorder Solutions helps you keep more of your money. See why AI is the rational choice, request a demo today. [crossborder.ai/20]

May 11, 2020
SaaStr 332: Initialized Capital Co-Founder and Managing Partner Garry Tan on The New Normal
22:40

Prepare for the worst, hope for the best. Hear from Garry Tan, co-founder and managing partner at Initialized Capital, about how to protect your business during a crisis. He'll cover remote work, team management, sales, marketing, product development and more.

May 07, 2020
SaaStr 331: The Right Way To Structure Enterprise Pipeline Reviews, How COVID Is Impacting New Enterprise Deals, How SaaS Companies Can Not Only Decrease Churn But Increase Upsell Today with Jessica Lin, Co-Founder @ Work-Bench
29:26

Jessica Lin is a Co-Founder and General Partner @ Work-Bench, one of New York’s leading early-stage enterprise funds with a portfolio including the likes of Cockroach Labs, X.ai, Dialpad, VTS and Catalyst to name a few. Prior to Work-Bench, Jessica was a Learning and Development Manager at Cisco Systems, where she worked with the Engineering organization on Agile transformation, innovation and culture. Jessica is actively involved with the education and workforce development community in New York City and as chair of the Industry Advisory Board at Opportunities for a Better Tomorrow.

 In Today’s Episode We Discuss:

  • How Jessica made her way from learning Swahili into the world of enterprise and into the world of venture with the founding of Work-Bench?
  • How should founders expect to see their new business pipe be impacted by COVID? What does Jessica believe is the right way to do proper pipe reviews? What specific elements does Jessica really double click on in reviews? Where does Jessica find managers and founders do pipe reviews wrong?
  • What does Jessica believe is the right way for sales reps to engage with new customers during this time? What is the right tone to adopt that achieves both empathy and a business objective? How should sales teams and CS respond to requests for discounts? What should be the compromise with discounts? 
  • What specific and deliberate things can startups do not just to prevent churn but also to increase usage and upsell? Does Jessica agree with the rule of thumb that in enterprise, on an annual basis, 95% of your customers should retain? What other strategies has Jessica seen work really well for retention?

Jessica’s 60 Second SaaStr:

  1. What would Jessica most like to change about the world of SaaS?
  2. What is the hardest element of Jessica’s role today with Work-Bench?
  3. The NYC ecosystem, pros and cons?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Jessica Lin 

Lower your burn by leveraging AI to claim R&D tax credits for a flat fee. Cash on hand is more important than ever, CrossBorder Solutions helps you keep more of your money. See why AI is the rational choice, request a demo today. [crossborder.ai/20]

May 06, 2020
SaaStr 330: TripActions CMO Meagen Eisenberg on Making Trade-Offs In Marketing
32:57

The true test of marketers. Are you a revenue driver or a cost center? You cannot afford to be the latter. Marketing leaders must focus their teams on the areas that will drive revenue while they cut costs - the biggest impact for the business. Join TripActions CMO Meagen Eisenberg at SaaStr Summit as she highlights her approach to ensuring Marketing delivers on its mission-critical role even in times of uncertainty or crisis.

Apr 30, 2020
SaaStr 329: How Renewals and Discounting Will Be Impacted by COVID & How Enterprise Founders Should Approach Capital Allocation & Efficiency Today with Navin Chaddha, Managing Director @ Mayfield
24:06

Navin Chaddha is the Managing Director @ Mayfield who just last month announced $750M in new funds split across their core and select funds. As for Navin, under his leadership Mayfield has raised over $2.2Bn in new funds and he has backed some of the best of the last decade including Poshmark, Lyft, Hashicorp, CloudGenix and more. During his career Navin has invested in 50 companies, 17 have gone public, 20 have been acquired. Prior to VC, Navin was an entrepreneur where he co-founded or led 3 startups, all of which had successful exits with one being acquired by Microsoft. 

 In Today’s Episode We Discuss:

  • How did Navin make his way into the world of venture from successfully founding and exiting 3 businesses? What made him take the jump into investing full-time from being an EiR?
  • How does Navin expect the B2B landscape to be impacted by COVID-19? How does Navin advise B2B founders to think about how renewals will be impacted? How does Navin advise founders to think through how to approach the topic of discounting with their customers? In what situations does Navin agree to provide discounts to customers?
  • How does Navin foresee the B2C landscape to be impacted? How does Navin advise founders to think through the level of aggression with which they pursue traditional marketing channels, now with much lower CACs? Will these CACs remain low priced? How does Navin expect company pricing to change over the next few months?
  • How has Navin seen himself evolve and change as a board member over the last decade? What have been his major moments of learning? What advice would he give to new board members joining their first boards? What can board members do to build a relationship of trust and intimacy with their founders? What works? What does not?

Navin’s 60 Second SaaStr:

  1. What does Navin know now that he wishes he had known when he entered the world of venture with Mayfield in 2004?
  2. What is the hardest element of Navin’s role with Mayfield today?
  3. What would Navin most like to change about the world of venture? Why?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Navin Chaddha

Apr 29, 2020
SaaStr 328: SaaStr CEO Jason Lemkin and Gorgias CEO Romain Lapeyre on What They're Seeing with SMB E-commerce Customers
22:51

Romain Lapeyre is CEO of Gorgias. Gorgias is the leading help center on the Shopify platform, and that gives them a pulse into a large segment of SMBs in particular. They have almost 2,500 customers in segments both struggling (fashion, luxury), and growing (electronics, etc.). They are coming up on $10m ARR but aren’t there quite yet, so a lot like a lot of you, or where you’ll be soon enough.

Apr 23, 2020
SaaStr 327: Domo's Chief Strategy Officer, John Mellor on Why COVID Will Do More For Digital Transformation Than Any Other C-Level Initiative, What Great Change Management Looks Like In Practice & How To Gain True Bottoms Up Adoption When Also Selling Top
32:02

John Mellor is Chief Strategy Officer @ Domo, the company that allows you to leverage BI at scale to empower your team with data. Prior to their IPO, Domo raised funding from the likes of Benchmark, Founders Fund, a16, Greylock and IVP to name a few. As for John, prior to Domo he served as vice president for strategy and business operations for Adobe’s Digital Experience business, driving more than $3 billion in annual revenue. John joined Adobe through the company’s acquisition of Omniture in 2009, where he served as executive vice president of marketing, driving all marketing efforts to strategically advance the industry’s largest standalone web analytics business.

 In Today’s Episode We Discuss:

  • How did John make his way into the world of SaaS over 2 decades ago and how did that lead to his running a $3Bn ARR business line at Adobe and lead to his joining Domo? What were John’s biggest takeaways from his decade at Adobe?
  • Why does John believe that COVID will be a bigger accelerant than any other C-level led initiative? For vendors going through that digital transformation with their customers, what is the right tone to adopt that is both empathetic and achieves business objectives? Is digital transformation a technology challenge or a behavioural challenge?
  • How will a 100% virtual event environment impact physical events when and if they do come back? What were John’s biggest takeaways from running Domo’s annual event virtually? What worked? What did not work? On a conversion basis, how did it compare to in-person events? How should we structure content for these virtual events?
  • How does John think about the role of leadership in a crisis such as this? What is the right tone for the leader to adopt? Where does John believe many leadership teams go wrong in times such as this? How can leadership teams ensure that a crisis is not self-fulfilling and how can one prevent that mindset?      

John’s 60 Second SaaStr:

  1. What does John know now that he wishes he had known when he entered the world of SaaS?
  2. What is the optimal relationship between the CEO and Chief Strategy Officer?
  3. What would John most like to change about the world of SaaS 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

John Mellor

Apr 21, 2020
SaaStr 326: Gusto COO Lexi Reese on The Playbook to Scaling High-Performance Teams
23:50

Gusto's Lexi Reese walks you through scaling high performance teams. Is trust earned or given? How do you communicate for impact?

Apr 16, 2020
SaaStr 325: How Marketing Teams Can Replace The Leads Lost From Events in A COVID World & The Right Tone To Adopt With Clients That Is Caring and Achieves Business Objectives with Carolyn Guss, VP Corporate Marketing @ PagerDuty
29:27

Carolyn Guss is VP of Corporate Marketing @ PagerDuty, the company keeping your digital operations running perfectly with their real-time operations platform. Prior to their IPO in April 2019, PagerDuty had raised funding from some of the best in the business including a16, Bessemer, Meritech, Harrison Metal and Elad Gil to name a few. As for Carolyn, prior to joining PagerDuty she spent 5 years as the GM of Method Communications San Francisco Office and before that spent time on the other side of the pond with a close to 7-year stint at Orange as Head of Corporate PR and Head of US Communications.

 In Today’s Episode We Discuss:

  • How Carolyn made her way across the pond from Head of US Communications at Orange to GM of Method in SF to then playing a key role in the marketing team at PagerDuty?
  • How does Carolyn think startups and larger companies can replace the leads that are lost from having no events in a COVID world? How are PagerDuty shifting their strategy? How does PagerDuty think about brand marketing? Does it have to be tied to a number directly tied to revenue? What are the challenges with brand marketing?
  • What does Carolyn believe is the right tone to approach customers within this time? How can one be supportive but also drive towards business objectives? In terms of tone, what is the right tone to approach the broader team with? How does PagerDuty gain a sense of company morale at scale? What tools do they use?   
  • How does Carolyn think about the benefits of transparency both with employees and with customers? Is there an extent to the benefits of transparency? Can one ever been too transparent? How does one think about this in a very corporate perspective with PagerDuty now being a public company?      

Carolyn’s 60 Second SaaStr:

  1. What does Carolyn know now that she wishes she had known at the beginning of her time in marketing?
  2. Hardest element of her role with PagerDuty today?
  3. Who is killing it in the world of SaaS marketing? Why? 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Carolyn Guss

Apr 14, 2020
SaaStr 324: SaaStr CEO Jason Lemkin and Bessemer Venture Partners' Partner Byron Deeter on The Current State of Venture Capital & Cloud
39:46

Join SaaStr CEO Jason Lemkin and Bessemer Venture Partners Partner Byron Deeter for a deep dive on what's going on in Venture Capital and Cloud.

Apr 09, 2020
SaaStr 323: The Core Challenges in Moving To Remote Work Overnight, What Does Great Change Management Look Like & The Optimal Position For Customer Success In The Organisation with Bhavin Shah, Founder & CEO @ Moveworks
31:05

Bhavin Shah is the Founder & CEO @ Moveworks, the cloud-based AI platform, purpose-built for large enterprises, that resolves employees' IT support issues⁠—instantly and automatically. To date Bhavin has raised over $108M with Moveworks from the likes of Mamoon Hamid @ Kleiner Perkins, Arij Janmohamed @ Lightspeed, Bain Capital, Sapphire Ventures and ICONIQ. Prior to Moveworks, Bhavin was the Founder and CEO @ Refresh which was later acquired by LinkedIn and then before that founded Gazillion Entertainment, a company he scaled to over 200 employees. 

 In Today’s Episode We Discuss:

  • How Bhavin made his way into the wonderful world of SaaS and came to found Moveworks?
  • What are the core challenges IT teams are facing as a result of the move to remote work? Where do many make mistakes here? What can one do from a structural perspective to set them up for success when moving to remote? 
  • What does great change management look like in Bhavin’s mind today? Where do so many go wrong here? How does this change in the world of remote? Who should be involved in executing on the change management plan?  
  • How does Bhavin think about the role of customer success today? Why does Bhavin believe that customer success and product should be in one org? How does Bhavin think about the interplay of marketing and customer success? Is marketing moving closer and closer to customer success with their content?      

Bhavin’s 60 Second SaaStr:

  1. What is the hardest element of Bhavin’s role with Moveworks today?
  2. Hardest role to hire for today? Why? 
  3. If Bhavin could change one thing in the world of SaaS today, what would it be?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Bhavin Shah

Apr 06, 2020
SaaStr 322: ICONIQ Capital General Partner Doug Pepper on Key Lessons from a $5B SaaS Category Leader
22:14

Many people make the false assumption that the path for a highly successful SaaS company is straight “up and to the right”. Of course, for those involved, the reality of the journey is characterized by a series of obstacles that must be navigated. Fmr. Shasta Ventures Doug Pepper will share the key challenges that were overcome to allow Marketo to become a $5B SaaS Category Leader in Marketing Automation.

Apr 02, 2020
SaaStr 321: Front CMO Anthony Kennada on Adapting Marketing Playbooks To Changing ACV's and Sales Cycles, The Right Way To Think About Brand Marketing and How To Fundamentally Build a Challenger Brand
30:55

Anthony Kennada is the CMO @ Front, the startup that provides your team with better email so they can treat every customer like your only customer. To date, Front have raised over $138M from some leading names including Sequoia, Eric Yuan @ Zoom, Ryan and Jared Smith @ Qualtrics, Michael Cannon-Brookes and Jay Simmons @ Atlassian and Frederic Kerrest @ Okta to name a few. As for Anthony, prior to Front Anthony was the founding CMO at Gainsight where he and his team are credited with creating the Customer Success category. At Gainsight Anthony and the team developed a new playbook for B2B marketing that fueled the company’s growth from $0 to over $100M of ARR. If that was not enough, Anthony is also the author of Category Creation: How to Build a Brand that Customers, Employees, and Investors Will Love. The book debuted as a number one new release on Amazon.

In Today’s Episode We Discuss:

  • How Anthony made his way into the world of SaaS starting in the sales team at Box and how that led to his entering the world of marketing and creating the customer success category?
  • How does Anthony marketing playbook change when making the move from Gainsight with higher ACV’s and longer sales cycles to Front with lowers ACV’s and much higher volume? How does Anthony think about ABM today with Front given the lower ACVs? At what ticket size does ABM make sense?
  • How does Anthony feel about brand marketing? Why did Anthony and Front decide now was the right time to engage with billboards? How does Anthony think about data and tracking for brand marketing? Does Anthony believe that all marketing has to be tied to a number directly related to revenue?  
  • How does Anthony seeing a changing relationship between customer success and marketing? How is marketing being pushed further into the realms of CS? What is the optimal relationship between CS and marketing? How does this compare to the relationship of sales and marketing more traditionally?       

Anthony’s 60 Second SaaStr:

  1. What does Anthony know now that he wishes he had known at the beginning of his time in marketing?
  2. What is the hardest element of Anthony’s role with Front today?
  3. Who does Anthony think is killing it in the world of marketing today?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Anthony Kennada

Mar 30, 2020
SaaStr 320: SaaStr CEO Jason Lemkin and Gainsight CEO Nick Mehta on What It Was Like in 2008-2009 and What We Can Expect for 2020
33:26

We’re obviously in a very unique situation today. The pace at which Corona is impacting us all right now is so fast, it’s hard to keep up.

Today is different from other times but in SaaS. It will probably be like ’08-’09 downturn — just faster.

Join Jason Lemkin, CEO and Founder of SaaStr, and Nick Mehta, CEO of Gainsight, as they take a look back at what happened to them as a SaaS vendor in ’08-’09, and what learnings you can leverage.

Mar 26, 2020
SaaStr 319: How To Think About And Make Pre-Emptive Burn Cuts, Operational Survival In Times Of Uncertainty & Managing Your Psychology As Founder & CEO with May Habib, Founder & CEO @ Qordoba
31:29

May Habib is the Founder & CEO @ Qordoba, the platform that helps everyone at your company write with the same style, terminology and voice. To date, May has raised over $21M in funding with Qordoba from the likes of Upfront Ventures, Aspect Ventures, Bonfire Ventures and Michael Stoppelman to name a few. Before entering the world of SaaS, May was a vice president at one of the world's largest sovereign wealth funds, where she was the first employee on the technology investment team, building a portfolio now worth over $20B. Before that, May started her career in the New York Office of Lehman Brothers raising capital for software companies.  

In Today’s Episode We Discuss:

  • How May made her way into the world of startups and SaaS from being a VP at one of the world’s largest sovereign wealth funds in the Middle East?
  • How does May think about and assess operational survival in times of such uncertainty? Why does this downturn feel so different to prior downturns? Operationally, what needs to fundamentally change about your processes?
  • How does May think about when is the right time to engage with pre-emptive burn cuts? Where does one look first in the organisation when making these cuts? How does one structure those discussions? What is the right way to do it? What is the right way to communicate the cuts to the team, customers and investors? 
  • How does one keep the existing teams spirits high when they have just seen many of their friends be released? What is the right way to manage those discussions? What can founders do to build unity in their team now everyone is WFH? What has worked well for the Qordoba team? Where do many go wrong here?       

May’s 60 Second SaaStr:

  1. What is the most challenging element of May’s role with Qordoba today?
  2. What does May know now that she wishes she had known at the beginning?
  3. If May could change one thing about the world of SaaS, what would it be and why?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

May Habib

Mar 23, 2020
SaaStr 318: Doctolib CDO Agnes Bazin on The Secrets to SMB Sales
21:15

The first step in success with SMB clients is to recognize that it’s not a one size fits all scenario. Companies need a specialized approach for SMB accounts, different than the tactics used for Enterprise. Andrei Brasoveanu will sit down for a conversation with Agnes Bazin Doctolib on how to create a targeted and effective sales process tailor-made for SMB.

Mar 19, 2020
SaaStr 317: How To Encourage, Grow and Track Word of Mouth Marketing, How The Rise of Product-Led Growth Changes The Structure of Sales and Marketing & The Biggest Takeaways on Paid vs Organic Marketing From Seeing The Hyper-Growth @ Slack with Rachel Hep
33:36

Rachel Hepworth is VP of Marketing @ Pilot, the startup that offers the best bookkeeping, tax and CFO services for growing businesses. To date they have raised over $58M from some of the best in the business including Index Ventures, John Collison, Paul English, Drew Houston, Frederic Kerrest, Diane Greene and more incredible names. As for Rachel, prior to joining Pilot, she saw the hyper-growth of Slack firsthand enjoying a couple of different roles including Head of Growth Marketing and then also Head of Self Service and Platform Marketing. Before Slack, Rachel spent 4 years at LinkedIn where she led the product marketing team for content experiences. Finally, before LinkedIn, Rachel spent close to 3 years at Climate Corporation, prior to their $1Bn exit to Monsanto. 

 In Today’s Episode We Discuss:

  • How Rachel made her way from marketing manager at Climate Corporation to VP of marketing at Pilot today? What were Rachel’s biggest takeaways from her time seeing the hyper-growth at Slack?
  • How does Rachel think about organic growth and inciting word of mouth today? How does Rachel think they can be more accurately tracked and measured? How does Rachel think about the optimal ratio of paid to organic in growth? Would Rachel agree in paid, your payback period doubles every $5M you spend?
  • With the rise of product-led growth, are we seeing a fundamental shift in the structure of sales and marketing? How does Rachel see marketing move ever close to the function of customer success today? What is the optimal way for customer success and marketing to work together? 
  • How does Rachel think about the importance of getting in front of your customers? Why does Rachel believe that data tells you the what and customer conversations tell you the why? What is the right way to structure your customer conversations? Where do so many people go wrong here?      

Rachel’s 60 Second SaaStr:

  1. Hardest element of your role with Pilot today?
  2. If Rachel could change one thing about SaaS today, what would it be?
  3. Who is killing it in SaaS marketing? Why?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Rachel Hepworth

Mar 16, 2020
SaaStr 316: MessageBird CEO Robert Vis on Early Gains, Early Pains: 5 Lessons for Surviving Hypergrowth
22:02

The startup journey moves in waves—whether you’re ready or not. After finding funding and product/market fit, your next steps as a founder in the hypergrowth phase can determine the future of your company. Harry Stebbings of Stride.VC and Robert Vis of MessageBird will walk through lessons learned to survive hypergrowth and what will make a difference when it comes to scaling. Hear how to navigate fast growth and how to look ahead as you travel forward.

Mar 12, 2020
SaaStr 315: Pipe Co-Founder, Harry Hurst on Creating A New Asset Class Securitising Software Contracts, Why Customer Success Is More Important Than Customer Acquisition & How To Think Strategically About Brand Building in SaaS Today
23:22

Harry Hurst is the Co-Founder & Co-CEO @ Pipe, the startup that gives you control of your cash flow by giving you access to the full annual value of your monthly subscriptions, upfront. This month they announced their $6M seed round led by David Saks @ Craft and joined by Fika, Weekend Fund, Naval Ravikant and WorkLife Ventures to name a few. Prior to Pipe, Harry co-founded Skurt raising over $11M in the process before being acquired by Fair.com. Harry has also angel invested in the likes of BreathePod and Try.com. 

 In Today’s Episode We Discuss:

  • How Harry made his way from the UK to founding one of Silicon Valley’s hottest SaaS startups with the founding of Pipe?
  • How does Harry think about when is the right time for a startup to raise VC funding? How does Harry stress test the alignment between the founder and the VC/ Opposingly, when is the right time for a founder to take non-dilutive capital from Pipe instead?
  • Pipe’s lending model is so centred around churn prediction, what does their churn analysis look like at Pipe? How does Harry think about the right way to structure churn post mortems? Why does Harry believe investing in customer success is far more important than customer acquisition? 
  • How does Harry think about the importance of brand for enterprise startups today? Do you have to invest in it from Day 1? What mistakes does Harry see many founders make when it comes to investing in their early brand?      

Harry’s 60 Second SaaStr:

  1. What does Harry know that he wishes he had known at the beginning?
  2. What does Harry believe is the hardest role to hire for today? Why?
  3. What does Harry believe that most around his disbelieve?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Harry Hurst

Mar 09, 2020
SaaStr 314: Showpad CMO Theresa O'Neil on Aligning Sales, Marketing, and CS to Scale Revenue and Retention
24:52

According to a study from SiriusDecisions, the majority of buyers (81%) today make purchase decisions based on buying experience, over product or price. To meet buyers’ high expectations and manage the challenging sales landscape, companies must involve their entire organization in maturing the sales process- including after prospects sign on the dotted line. This session will outline a practical approach to growing revenue and retention by aligning sales, marketing, and customer success.

Mar 05, 2020
SaaStr 313: What The World's Largest SaaS Incumbents Taught Me About Founding & Scaling SaaS Businesses
22:13

Today we deep dive into what startups can learn from the large SaaS incumbents of today. 

Sara Varni: CMO @ Twilio on her biggest takeaways from her time at Salesforce.

Erica Schultz: President of Field Operations @ Confluent on her biggest takeaways from her time at Oracle.

Whitney Bouck: COO @ Hellosign on her biggest takeaways from her time at Box.

Leyla Seka: Partner @ Operator Collective on her biggest takeaways from her time at Salesforce.

Ryan Bonnici: CMO @ G2 on his biggest takeaways from his time at Salesforce.

Ryan Barretto: SVP @ Sprout Social on his biggest takeaways from his time at Salesforce

Tien Tzuo: Founder & CEO @ Zuora on his biggest takeaways from his time at Salesforce.

Paul Albright: Board member @ Clarizen on his biggest takeaways from his time at SuccessFactors.

Jaleh Rezaei: Founder & CEO @ Mutiny on her biggest takeaways from her time at Gusto.

Eugenio Pace: Founder & CEO @ Auth0 on his biggest takeaways from his time at Microsoft.

Liat Bycel: VP @ Airtable on her biggest takeaways from her time at Twitter.

Mark Goldberg: Partner @ Index on his biggest takeaways from his time at Dropbox.

 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Mar 02, 2020
SaaStr 312: Wrike CEO Andrew Filev on 5 Do's and Don'ts From My Bootstrapping Days
27:46

Starting a company can be daunting, exhausting, and expensive, but with the right focus and idea - extremely rewarding; take it from Andrew Filev, Founder and CEO of Wrike. In this session, he will outline the do's and dont's that he learned bootstrapping Wrike. Where it makes sense to invest your precious resources when to outsource, and how to save yourself money without cutting corners.

Feb 27, 2020
SaaStr 311: When To Hire Generalists vs Specialists, How To Retain Agility With Scale and Process and How To Always Keep Your Hiring Funnel Full with Karl Sun, Founder & CEO @ Lucidchart
31:56

Karl Sun is the Founder & CEO @ Lucidchart, a visual workspace that combines diagramming, data visualization, and collaboration to accelerate understanding and drive innovation. To date, Karl has raised $114M with Lucidchart from some of the best in the business including K9 Ventures, Meritech, Iconiq, GV and Kickstart in Utah. As for Karl, prior to founding the company he spent 6 years at Google in some fascinating roles including Head of Patents, Head of Business Development in China and running Google’s energy investments. As a result of his success, Karl was recently announced as EY’s Entrepreneur of the Year. 

 In Today’s Episode We Discuss:

  • How Karl made his way into the world of SaaS with the founding of Lucidchart having been Head of Business Development for Google in China and Head of Patents?
  • How does one know when we need to hire generalists vs specialists? How does this requirement change as the company scales? How does Karl fundamentally think about finding great talent and keeping top of funnel full? How does Karl think about working with recruiters? What works? What does not work?
  • Karl has been in every interview for every new hire for the first 6 years of the business, why? How does Karl think about doing this at scale? How does Karl structure the hiring process today? Why do they have a hiring committee? What does the process look like? How do they assess and test for culture?  
  • How does Karl think about retaining agility and flexibility with scale? How does Karl maintain employee empowerment with the implementation of process? How does Karl think about the balance between creating accountability without a fear of failure? What are the challenges of this?     

Karl’s 60 Second SaaStr:

  1. What is the hardest role to hire for today? Why?
  2. Hardest element of karl’s role as CEO today? Why?
  3. What does Karl know now that he wishes he had known at the founding of the company?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Karl Sun

Feb 24, 2020
SaaStr 310: EZPR Founder Ed Zitron on the Secrets of PR
21:43

SaaStr CEO Jason Lemkin and EZPR Founder Ed Zitron sit down to talk about all things PR. Who actually gets into these outlets? Is PR just pitching and getting articles? Take a listen for more.

Feb 20, 2020
SaaStr 309: David Skok on The 9 Stage Model To Get A B2B Company To Get Repeatable, Scalable & Profitable Growth
50:41

David Skok is a General Partner @ Matrix Partners, the firm with a portfolio including the likes of Hubspot, ZenDesk, Quora, CloudBees and more incredible companies. As for David, he started his first company in 1977 aged just 22. Since then David has founded a total of four separate companies and performed one turn-around. Three of these companies went public. David then joined Matrix from SilverStream Software, which he founded in June 1996. Prior to its July 2002 acquisition by Novell, SilverStream was a public company that had reached a revenue run rate in excess of $100M, with approximately 800 employees and offices in more than 20 countries around the world. David is also the author of foreentrepreneurs.com the must read blog in the world of SaaS metrics. 

 In Today’s Episode We Discuss:

  • How David made his way into the world of SaaS at the age of 22? How David went from founding 3 public companies to entering the world of venture with Matrix? Does David agree, “entrepreneurship does not get easier with time, it just gets different”?
  • What does David believe is the crucial step missing in B@B when it comes to finding product market fit? What is the most common mistake B2B companies make in the hunt for PMF? How should founders think about budget and resource allocation in this search for PMF? When is to early to measure unit economics and CAC?
  • How does David think about scaling sales teams? How does one know when is the right time to hire your first sales reps? What content and learnings should you have in place when you make the hire? How does David think about payback period on a per rep basis? What have been his lessons on optimising payback period for sales reps?  
  • What numbers is David looking for when it comes to payback period? Why is 12 months so crucial? How should founders think about sales rep compensation? What have been David’s learnings on how to integrate sales and marketing so tightly? How does marketing and customer success intertwine to be successful?     

David’s 60 Second SaaStr:

  1. Who is the best board member David has sat on a board with? Why?
  2. What advice would David have for me having just joined my first board?
  3. What would David most like to change about the world of tech and SaaS today?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

David Skok

Feb 17, 2020
SaaStr 308: RevenueCat CEO Jacob Eiting on Managing Millions in Mobile Subscriptions While Growing 20% a Month
25:19

RevenueCat is managing tens of millions of dollars in mobile subscriptions and growing 20% a month. Most of us think a lot about standard b2b and Cloud subscriptions, but we’re still new to the issues, challenges and opportunities in mobile subscriptions.

Feb 13, 2020
SaaStr 307: What Gusto Taught Me About How To Build and Maintain Great Culture, The Biggest Problem in B2B Marketing & How To Truly Determine The Effective of Marketing Today with Jaleh Rezaei, Founder & CEO @ Mutiny
32:36

Jaleh Rezaei is the Founder & CEO @ Mutiny, the startup that allows you to personalise your website for each and every visitor. Jaleh has raised from some of the best in the early stage business with Mutiny including the likes of Y Combinator, Uncork Capital and Cowboy Ventures on the fund side and then Mathilde @ Front, Henrique @ Brex and Shan-Lyn Ma @ Zola on the operator side. Prior to founding Mutiny, Jaleh spent an incredible 4 years at Gusto seeing their hypergrowth first hand as one of the first 10 employees. If that was not enough, Jaleh has also enjoyed advisory roles at both Google and Y Combinator. 

In Today’s Episode We Discuss:

  • How Jaleh made her way into the world of SaaS as one of the first team members at Gusto and how that led to her founding Mutiny most recently? 
  • What were Jaleh’s biggest takeaways from her time at Gusto? How did that time impact her operating mentality with Mutiny today? How did her time at Gusto teach her about the right way to build company culture? Where do so many go wrong with this?
  • What does Jaleh believe is the biggest problem in SaaS marketing today? How does Jaleh specifically use ABM to acquire customers and leads effectively? What price points is required for an ABM strategy to be viable?  
  • How does Jaleh approach the issue of determining the success of marketing? Should marketing be held accountable to a number tied directly to revenue? How does brand marketing play into this? Where are the nuances here?     

Jaleh’s 60 Second SaaStr:

  1. What is the hardest role to hire for today?
  2. Hardest element for Jaleh of her role with Mutiny today?
  3. What does Jaleh know now that she wishes she had known when she entered the world of SaaS?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Jaleh Rezaei

Feb 11, 2020
SaaStr 306: Bessemer Ventures Partner Alex Ferrara on State of the Cloud 2019: Europa Edition
22:39

Join Bessemer Venture Partners' Alex Ferrara as he takes a look at trends and predictions for the cloud industry in 2019. One of the most popular sessions from SaaStr Annual, this presentation will provide an in-depth look at the cloud computing industry across Europe and globally.

Feb 06, 2020
SaaStr 305: Lessons From Scaling Box From 5 Employees To IPO & The Right Way For Startups To Approach Partnerships with Karen Page, General Partner @ B Capital Group
35:33

Karen Page is a General Partner @ B Capital Group with a portfolio including the likes of Bird, Branch, Icertis, Evidation Health and Ninja Van to name a few. Prior to joining the world of venture, Karen was a Senior Director at Apple and before Apple, Karen spent an incredible 9 years at Box as a founding member of the executive team, where she was responsible for defining and leading Box's Industry GTM strategy. Plus, from 2007 until 2013, Karen ran all of Box's business development, partnership, and strategic alliance activities. If that was not enough, Karen is also on the board of some incredible companies including Deputy and Plastiq. 

In Today’s Episode We Discuss:

  • How Karen made her way into the world of SaaS as one of the first employees at Box and then how that led to her transition to the world of investing with B Capital? 
  • What were Karen's biggest takeaways from seeing the hyper-scaling at Box? How did helping Aaron raise the Series B and onwards inform her view of what it takes to raise funding from the best SaaS investors? How does Karen think her mindset will shift when making the move from angel to now institutionally investing with B Capital?
  • When does Karen think is the right time for startups to think about partnerships? What questions should they ask in the “dating” phase of a potential partnership? What are the red flags? Does Karen agree that signing a massive partner too early can be dangerous? What does Karen recommend in terms of getting in front of the best CIOs? 
  • Is Karen concerned by the compression of fundraising timelines? How does Karen meet entrepreneurs before they go out to raise? How does Karen advise founders when it comes to the question of whether they should always be raising or not?     

Karen’s 60 Second SaaStr:

  1. What does Karen know now that she wishes she had known entering the SaaS industry?
  2. What is Karen’s favourite book? Why?
  3. Can a partnership be too big too early for a startup?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Karen Page 

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Feb 03, 2020
SaaStr 304: CircleCI CRO Jane Kim on Scaling up Your Sales Managers: 5 Mistakes New Leaders Make
27:39

If your SaaS business has a sales team, there’s no way to grow 100% year-over-year without also growing your sales leadership. In this talk, CircleCI VP of Revenue Jane Kim will talk about the 5 mistakes all new sales leaders make. Knowing the common pitfalls won’t stop you or your team from making them, but it will help build the most important skill any manager can have: resiliency. Come and learn how to build great leaders so you can grow your team, and ultimately, your business.

Jan 30, 2020
SaaStr 303: What It Takes To Build Dev Communities and Early Developer Adoption, How To Structure Trials and Freemium For Optimum Success and The 4 Different Pricing Variables To Consider with Eugenio Pace, Founder & CEO @ Auth0
34:19

Eugenio Pace is the Founder & CEO @ Auth0, the startup that allows you to rapidly integrate authentication and authorization for web, mobile, and legacy applications so you can focus on your core business. To date, Eugenio has raised over $213m with Auth0 from some of the best in the business including Meritech, Sapphire, Manu Kumar @ K9, Bessemer and Trinity. Prior to founding Auth0, Eugenio spent an incredible 12 years at Microsoft leading the Program Management team in the patterns & practices group at Microsoft.

In Today’s Episode We Discuss:

  • How Eugenio made his way into the world of startups with the founding of Auth0? What were his biggest takeaways from 12 years watching the hyper-growth of Microsoft first hand? 
  • How does being a developer-first product fundamentally change the go-to-market? Who has done this best over the last few years? What have they done that has allowed them to scale faster than others? What has been Eugenio’s takeaways in what works when building developer communities and early developer adoption?
  • How does Eugenio respond to the common thinking that “devs don’t have the budget”? Does this limit your ability to expand into large ACVs once in an organisation? How does Eugenio approach the issue of agency when selling to CIOs but having devs use the product? 
  • What have been Eugenio’s biggest lessons in what it takes to make a freemium product successful? How does one know how much of the secret sauce to giveaway? How does Eugenio approach pricing today through 4 different variables? How does Eugenio adopt a variable pricing mechanism that does not discourage usage?     

Eugenio’s 60 Second SaaStr:

  1. Quality or quantity of logos in the early days?
  2. What does Eugenio know now that he wishes he had known at the beginning of his time at Auth0?
  3. What is the hardest element of his role today as CEO? What is he doing to really upscale there? 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Eugenio Pace

Jan 27, 2020
SaaStr 302: New Relic CCO Roger Scott on 7 Tips and Tricks to Having Happy Customers at Scale
26:07

Customer expectations are at an all-time high, making it more and more difficult for companies to please them. Companies who understand their customers well are the ones who rise to the top over their competitors. New Relic, provider of real-time insights for software-driven businesses has this formula figured out. Hear from Roger Scott, New Relic's EVP and Chief Customer Officer as he shares his 7 tips and tricks for keeping your customers happy— and how to do so at a large scale.

Jan 23, 2020
SaaStr 301: BigID’s Founder Dimitri Sirota on Raising $105M In The Last 5 Months of 2019, How To Know When To Pour Fuel On The Fire & How Founders Should Think About Runway and If There Is Cash On The Table, Whether You Take It?
26:54

Dimitri Sirota is the Founder & CEO @ BigID, the startup that provides advanced data discovery and intelligence for the data centre and cloud. To date Dimitri has raised over $145M for BigID from some of the best in the world of enterprise including Boldstart, Scale Venture Partners, Bessemer, Salesforce Ventures and Tiger Global who just a couple of weeks ago, led their latest $50M Series C. Before to BigID, Dimitri founded 2 prior businesses, the first in 1999 being a VPN security company called eTunnels and then the second being Layer Technologies where Dimitri enjoyed an incredible 10 year journey leading to their acquisition by CA Technologies in 2013. Dimitri is also an angel investor with a portfolio including Zume Pizza, Modalyst and TalentClick. 

In Today’s Episode We Discuss:

  • How Dimitri made his way into the world of enterprise software and came to found BigID as his third company? 
  • What specifically would Dimitri advise founders when the interests of their investor are not aligned to theirs? What is the right way to manage that situation? Does Dimitri believe that founders should always be raising? Does Dimitri believe when the money is on the table, you should take it? What is the right way for founders to think about valuation? 
  • What did the fundraising journey look like for BigID? What situation does every founder want to put themselves in? How does Dimitri think about runway and using fundraising for optionality? What does Dimitri make of the rise of pre-emptive rounds? How does Dimitri determine when is the right time to pour fuel on the fire?     

Dimitri's 60 Second SaaStr:

  1. What is his biggest strength and biggest weakness as a CEO?
  2. Who was the first check in BigID? How did the check come about?
  3. What does Dimitri believe that most around his disbelieve? 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Dimitri Sirota

Jan 20, 2020
SaaStr 300: Algolia CTO Julien Lemoine on a Founder's Guide to Scaling Applications: When to Build, When to Buy and What Breaks
25:10

When it comes to seamlessly scaling your applications, a top-notch engineering team will be your foundation. Next comes the decisions to build or buy your infrastructure, DNS, monitoring, and analytics tools. Julian Lemoine, Co-Founder, and CTO of Algolia will share his lessons learned on how to stay focused and innovative as you scale while also avoiding the innovation for innovation’s sake pitfalls.

Jan 16, 2020
SaaStr 299: Automation Anywhere CIO, Yousuf Khan on The Big Green and Red Flags When Pitching CIOs Today, How To Approach Pricing Discussions with CIOs & How to Make Procurement Processes Successful
34:04

Yousuf Khan is the Chief Information Officer @ Automation Anywhere, the only web-based and cloud-native RPA platform. To date, Automation Anywhere has raised over $840m in financing from Salesforce Ventures, Workday, General Atlantic and NEA to name a few. Prior to Automation Anywhere, Yousuf was the CIO & VP of Customer Success @ Moveworks. During his time at the company, they raised over $108m from Lightspeed, ICONIQ, Kleiner, Sapphire and Bain Capital. Before Moveworks, Yousuf was CIO @ Pure Storage during their period of hypergrowth both as a private and public company. Finally, before Pure, Yousuf’s first role in the valley was with Qualys again as CIO where he owned the entire global IT budget.   

In Today’s Episode We Discuss:

  • How Yousuf made his way from the UK to the valley and how that led to his becoming one of the leading CIOs today in the rising prominence of CIOs in enterprise? 
  • What are the biggest green lights for CIOs when startups are pitching them? Why does Yousuf believe now more than ever, the buyer experience is more important than the price? What makes for the best buyer experience for the CIO? What are the biggest red flags CIOs see when startups are pitching them? What must startups always remember when pitching CIOs?
  • How does Yousuf advise CIOs to approach pricing strategy when pitching CIOs? What must startups remember about how CIOs think about price? What other elements of the contract should startups really spend a lot of time focusing on? Where do founders make mistakes in negotiation? What can they do to enforce a sense of urgency when signing new clients?  
  • What can startups do to actively work with procurement teams and make the process as fast as possible? How does Yousuf advise founders to think about customised procurement requests to fit certain buyers? What do CIOs really want to see in the form of security and compliance? How can startups clearly and articulately present their plans for security, compliance and change management?     

Yousuf’s 60 Second SaaStr:

  1. Who does Yousuf think is killing it in the world of CIO’s today? Why?
  2. What is the ideal relationship between the CIO and the CEO?
  3. What are the core reasons buying processes take longer? 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Yousuf Khan

Jan 13, 2020
SaaStr 298: Podium CEO Eric Rea on Scaling Outside Silicon Valley: Going from $0 to $60M ARR in 4 Years
23:37

Startup success is not exclusive to Silicon Valley. With more companies launching and thriving outside of Silicon Valley, regions such as ‘Silicon Slopes’ in Utah and ‘Silicon Alley’ in New York City are gaining traction within the startup scene. Podium, an interaction management platform for local businesses, was founded in Utah and grew from five employees in 2015 to more than 300 in 2019 to become one of the fastest-growing SaaS companies in the United States. In just four years, Podium has raised almost $100 million, with annual recurring revenue increasing to almost $60 million. Eric Rea, CEO of Podium, will share how he grew the company he launched from his spare bedroom into one of the fastest-growing SaaS companies in the country.

Jan 09, 2020
SaaStr 297: Why Channel Partnerships Can Be The Biggest Accelerant To Your Business, How To Hire for Channel Partnerships and The Biggest Mistakes SaaS Founders Make In The Early Days with Bob Moore, Founder & CEO @ Crossbeam
35:52

Bob Moore is the Founder & CEO @ Crossbeam, the startup that helps companies find overlapping prospects and customers while keeping the rest of their data private and secure. To date Bob has raised over $15m with Crossbeam from friends of the show including Andy @ Uncork, Matt @ Firstmark, Bill @ First Round and Matt @ Salesforce Ventures, to name a few. Prior to Crossbeam, Bob founded Stitched, a powerful ETL service built for developers that was acquired by Talend in 2018. Before that Bob co-founded RJ Metrics, where he built a global base of online retailers leading to their acquisition by Magento Commerce in 2016. 

In Today’s Episode We Discuss:

  • How Bob made his way into the world of SaaS and came to found Crossbeam?
  • As an entrepreneur, Bob has previously said, “no one is coming to save you”. What did he mean by this? What were the core mistakes that he made with RJ Metrics? Is it the responsibility of the board to course correct at this early stage? How does Bob determine whether to be visionary and determined vs realising when something is not working?
  • Does Bob agree with the notion that channel sales have completely died in the world of SaaS? Why is this? What are the drivers of it’s death? How important is it to own the entire customer journey? At what scale does that become impossible? In terms of replacement, what does Bob believe will be the emerging trends in SaaS Go To Market that will replace it? 
  • How does Bob think about when is the right time to hire a Head of Partnerships? In the early days, partnerships can be a distraction, how does Bob determine between right and wrong when determining whether to engage in a partnership? Where do most startups go wrong both in hiring for partnerships and in the engagements themselves? 

Bob’s 60 Second SaaStr:

  1. What is the hardest element of Bob’s role with Crossbeam today?
  2. What does Bob believe that most around him disbelieve?
  3. What does Bob know now that he wishes he had known at the beginning?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Bob Moore

Did you know that if your network goes down it can cost you on average $5,600/minute? What if I also told you, you could have 100% confidence that your business data is secure and allow for  new employees to be on-boarded with ease and offboarded securely in a few short clicks. Your employees automatically have the right applications installed with the right permissions and joy of joys, you never hear about printer issues. Plus it’s all done through a first of its kind IT platform called Electric, delivering enterprise-grade IT support previously not available to small and medium-sized businesses at a fraction of the cost. So whether you have IT in-house or no IT at all, Electric solve it at lightning-fast speed either remotely or sending a certified partner to you. So if you’re interested in deploying world-class IT which keeps your employees productive and data secure visit: www.electric.ai/saastr

Jan 06, 2020
SaaStr 296: Cloudflare Head of Products Jen Taylor on 5 Steps to Launching a Product
15:57

The vision of exceeding sales, establishing credibility and successfully launching a product is no small task, especially when striving for that perfect introduction into the world of consumers. With so many articles, investors, and outside opinions, the true, simple tasks of launching can get lost in the noise. In this session, Jen Taylor, Head of Products at Cloudflare, will share her expertise and teach you to forget the noise, stick to the basics, and use 5 easy steps to turn that idea into a reality.

Jan 02, 2020
SaaStr 295: Most Downloaded VC Episode of 2019 with Tom Tunguz, General Partner @ Redpoint Ventures
35:02

This interview originally aired as Episode 213 on February 26, 2019.

Tom Tunguz is General Partner @ Redpoint Ventures, the venture fund with a portfolio including the likes of Stripe, Netflix, Zuora, Hashicorp and Juniper Networks just to name a few. As for Tom, he joined Redpoint in 2008 and has since led investments in Kustomer, Looker, Expensify and Gremlin all prior guests on the show I hasten to add. He is also the co-author of Winning with Data: exploring the cultural changes big data brings to business. Tom has also been named on the Forbes Midas Brink list. Before joining Redpoint, Tomasz was the product manager for Google’s AdSense social-media products and AdSense internationalization.

In Today’s Episode We Discuss:

  • How Tom made his way from creating software with his father in Brazil to being GP and forefront figure in the SaaS investment community as a GP at Redpoint today?
  • Annual contracts: To what extent do annual contracts dominate today? How does this differ when comparing enterprise to SMB? Why does Tom think in the early days one should be wary of signing too many multi-year contracts? What are the dangers there? How does Tom think about calculating churn when it comes to multi-year contracts?
  • What were the findings on what good looks like when it comes to logo retention? How does this differ when comparing SMB to enterprise? What were the commonalities of leading indicators of churn? Is it fair to always surmise that when serving SMB one will always have a higher rate of churn? What is the right way to conduct a churn analysis?
  • Assisted vs unassisted: What does Tom believe are the leading benchmarks for both? How does this differ when comparing SMB to enterprise? How does the impact of a salesperson change the conversion rate? What time frame from SAL to closed lead suggests product market fit? What one question must all founders be asking in the sales process? 
  • How does Tom think about constructing comp plans the right way today? How should comp plans differ when comparing AEs to customer success? Where should the responsibility for upsell lie, customer success or sales? Should sales commission be paid on renewals?  

Tom’s 60 Second SaaStr:

  1. What does Tom know now that he wishes he had known at the beginning?
  2. What is Tom’s favourite book and why?
  3. What is Tom’s most recent investment and why did he say yes?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Tom Tunguz

 

Dec 30, 2019
SaaStr 294: Egnyte CCO Rajesh Ram on Land, Expand, Explode: How to Win the Long-Game in SaaS
23:39

The SaaS business model has risen to popularity for many reasons - it’s fast-paced, creates residual revenue streams, and well, the multiples are strong. However, while many are flocking to reap the benefits of the SaaS model, truly understanding how it works sustaining success over time is not as easy as some make it look. Rajesh is going to walk you through the key elements of winning the long game in SaaS - how to win customers, how to create long-term relationships, and how to avoid churn. He will also provide insights on the differences between commercial and enterprise customers and the key metrics to keep an eye on as you grow your business.

Dec 26, 2019
SaaStr 293: OpenView Partner Ashley Smith on Using Product Led Growth as an Indicator for Investment
19:19

Congratulations you’ve built a product that’s proven itself in the marketplace! So how can you leverage that product’s success to obtain the valuation and funding you need to scale? Ashley Smith, Venture Partner at OpenView will provide insight on what investors are looking for in product metrics and growth indicators so you can capitalize on your product's story for funding.

Dec 19, 2019
SaaStr 292: Most Downloaded Founder Episode of 2019 with Manny Medina, Founder & CEO @ Outreach
27:06

This interview originally aired as Episode 229 on April 29, 2019.

Manny Medina is the Founder & CEO @ Outreach, the market leading sales engagement platform that turns your team into a revenue driving machine. To date, Manny has raised over $114m in funding from some great people including friends of the show in the form of Alex Clayton @ Spark, Mayfield, Trinity Ventures and DFJ Growth, just to name a few. Prior to founding Outreach, Manny spent 7 years with Microsoft where he ran the Latin America and Canada business development group for Microsoft’s emerging mobile division, representing $50M of yearly revenue. Befofe that Manny was a Senior Product Manager @ Amazon where he engineered the compensation system for Amazon Associates and Web-Services which accounts for 15% of Amazon's traffic. 

In Today’s Episode We Discuss:

  • How Manny made his way to found the leader in sales engagement from product management at Amazon and Business Development @ Microsoft.
  • How does Manny fundamentally approach managing top of funnel? What are the 2 big dangers of not managing it aggressively? What can be done to ensure not only full but high quality top of funnel? 
  • Why does Manny believe it is so important to track pipeline coverage as one of your core metrics? What does good look like when it comes to pipeline coverage? How does this change if you are creating vs in an existing market? How does Manny think about specialisation within the sales function? Why are SDR’s 99% of the time not able to carry leads to completion? 
  • How does Manny think about quota construction today? Does Manny err on the side of setting high to be ambitious or setting low to increase confidence? How can managers really empower their reps to be aggressive in hitting their quota and exceeding it? How does Manny think about resource allocation on the individual rep level? What is sufficient? What is excessive?
  • Does Manny believe that the founder should always be responsible for selling their product at one moment in time? How did Manny sell the first $1m in ARR simply through walking the streets of SOMA and selling door-to-door? What were his biggest lessons from doing this?  Why does Manny believe that you should not have a VP before $5m? 

60 Second SaaStr:

  1. What does Manny know now that he wishes he had known in the beginning?
  2. What does the future of sales prospecting look like to Manny?
  3. What would Manny like to change about the world of SaaS today?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Manny Medina

Dec 16, 2019
SaaStr 291: LucidChart CEO Karl Sun on Top Lessons Learned From Our Best and Worst Marketing Experiments
24:28

Lucidchart has been recognized as one of the most mature Product Lead Growth business models in the market, driving over 700,000 registrations per month, combined with a hyper-efficient B2B business model. It didn’t happen by accident. It happened through experimentation: from extensive A/B testing (with over 500 marketing tests completed in 2018), to testing crazy brand videos (which have garnered over 200 million views and was named the only ad campaign that truly mattered in 2018 by Adweek), to constant iteration and expansion of the business model.

Experimental marketing brings together the science and art of marketing, allowing for creativity that drives results. It’s an essential skill in the toolkit of the modern marketer, and one that’s easy to get started with, no matter your company scale.


Key Takeaways:

- Discover how to start or extend your marketing experimentation.
- Learn how marketing experimentation can apply across funnels, brands, and business models.
- Get tips on how to build a culture of experimentation that fosters creativity and drives business results.

Dec 12, 2019
SaaStr 290: How To Sell To CIOs Successfully; Discounting, Freemium, Trials, Multi-Year Contracts, Transparency on Product Roadmap; The Ultimate Guide with Yousuf Khan, Serial CIO, Startup & VC Advisor
36:31

Yousuf Khan is a serial CIO, start-up and VC advisor. Most recently Yousuf was the CIO & VP of Customer Success @ Moveworks, the advanced AI built for enterprise providing automatic resolution of IT issues. During his time at the company, they raised over $108m from Lightspeed, ICONIQ, Kleiner, Sapphire and Bain Capital. Pre Moveworks, Yousuf was CIO @ Pure Storage during their period of hypergrowth both as a private and public company. Finally, before Pure, Yousuf’s first role in the valley was with Qualys again as CIO where he owned the entire global IT budget.   

In Today’s Episode We Discuss:

  • How Yousuf made his way from the UK to the valley and how that led to his becoming one of the leading CIOs today in the rising prominence of CIOs in enterprise? 
  • How open and can transparent can CEOs be with CIOs? Do CIOs know the state of early-stage companies in terms of their cash situation, fundraising etc? Does that ever put them off buying? What is the right tone and temperament to take with those CIOs in the first meetings? How does Yousuf advise founders on quality or quantity of logos in the early days? 
  • How does Yousuf advise CEOs approach CIOs when it comes to discounting? Do they make a difference to the buying decision of the CIO really? Should founders offer discounts in exchange for customer testimonials? How can CEOs provide alternative forms of social validity to other CIOs in the ecosystem, other than case studies?  
  • How does Yousuf advise founders approach CIOs when it comes to multi-year deals? Does the mindset of the CIO change when the deal is paid upfront? How should the founders position that? When it comes to implementation, how important is time to value in the mind of the CIO? What is the worst thing a founder can do when discussing implementation?    

Yousuf’s 60 Second SaaStr:

  1. What separates good from great when it comes to CIOs?
  2. What makes the best board members?
  3. What are Yousuf’s biggest strengths and weaknesses?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Yousuf Khan

Dec 09, 2019
SaaStr 289: Salesloft CEO Kyle Porter, Zoom Head of Sales Ops Hilary Headlee and FireEye VP of WW Commercial SalesChristina Foley on 7 Key Tips & Tricks to Getting More Revenue Per AE
23:26

Salesloft CEO Kyle Porter, Zoom Head of Sales Ops Hilary Headlee and Fireeye VP of WW Sales Christina Foley share the seven tips and tricks to getting more revenue per AE.

Dec 05, 2019
SaaStr 288: Why Marketing Is The Gatekeeper of Customer Experience, The Relationship Between Customer Success and Marketing Today & How To Reduce Friction in The Hand-Off From Marketing to Sales with Des Cahill, CMO @ Oracle CX Cloud Suite
36:34

Des Cahill is the Chief Marketing Officer for Oracle CX Cloud Suite, an integrated set of marketing, sales, commerce and service solutions that power customer experience for thousands of leading global brands. Prior to Oracle, Des was the CMO @ Kerio Technologies marketing to over 60,000 SMB customers and 5,000 channel partners. Before Kerio, Des was the CMO @ Ensighten, where he helped grow the customer base from 10 to 100 and revenues from $2M to $14M. Des has also spent time as CEO having founded and grown Habeas Inc from 0 to 450 customers, $9M in revenue and raising 3 rounds of venture financing. 

 In Today’s Episode We Discuss:

  • How Des made his way into the world of startups and came to be CMO of Oracle’s CX Cloud suite? 
  • Why does Des believe customers are more unpredictable now than ever before? How is their behaviour fundamentally changing? What are some great examples of how Des has seen companies amend to the changing consumer demands?
  • How does this change the role of the marketer today? How does this change the prioritisation of customer experience for marketers? What are the challenging elements of this change? How does the role of marketing also integrate with the post-sale and customer success with much of their content being used there?  
  • How does Des think about the relationship between marketing and sales teams? What are Des’ biggest tips on how to reduce friction in the handoff from marketing to sales? What works? What does not work? What is the right OKR to measure marketing teams? Does it have to be tied directly to revenue?  

Des’ 60 Second SaaStr:

  1. Biggest breakdown in the working of an efficient funnel?
  2. Who is killing it in SaaS marketing today and why?
  3. Advice in SaaS you commonly hear but disagree with?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Des Cahill

Dec 02, 2019
SaaStr 287: Slack's Head of NA Sales Kevin Egan and Head of Mid-Market Sales Dannie Herzberg on going From Freemium to Enterprise
22:32

Kevin Egan, Slack's VP of North American Sales and Dannie Herzberg, Slack's Director of Sales as discuss their strategies for going from Freemium to Enterprise at Slack.

Nov 28, 2019
SaaStr 286: The Biggest Sales Hiring Mistakes and Lessons From Them, How To Win At Hosting B2B Events & How To Apply True Customer Segmentation and Focus To Your Customer Base with Allie Janoch, Founder & CEO @ Mapistry
32:42

Allie Janoch is the Founder & CEO @ Mapistry, the startup that makes environmental compliance simple. As for Allie, prior to founding Mapistry she started her career in MIT’s Lincoln Lab before joining IQ Engines (acquired by Yahoo). Post acquisition, Allie integrated the technology built at IQ Engines into Flickr search. 

 In Today’s Episode We Discuss:

  • How Allie made her way from the world of Yahoo to founding the game changer of environmental compliance in Mapistry? Having had both big company, small startup and founding experience, what would Allie advise new graduates entering the workforce today? 
  • What were the biggest mistakes that Allie made when it comes to sales hiring? What were the learnings from those mistakes? How does Allie advise other founders on scaling sales teams? How does Allie think about sales rep payback period? How can one determine the effectiveness of a sales rep when they are engaging in 9-12 month sales cycles?
  • How does Allie think about the importance of focus applied to customer segmentation today? How does Allie measure true customer success? NPS? Churn? Product analytics? How does Allie explain the macro market size to VCs when they initially see the small customer segment?  
  • Why did Allie start doing their own events with Mapistry? How should startups think about whether events are the right strategy for them or not? How should founders think about resource allocation and budget when it comes to events? How does Allie measure the ROI of events? 

Allie’s 60 Second SaaStr:

  1. What does Allie know now that she wishes she had known at the beginning? 
  2. What would Allie most like to change about the world of tech and Silicon Valley?
  3. What is the biggest challenge for Allie today with Mapistry?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Allie Janoch

Nov 25, 2019
SaaStr 285: Adyen CCO Roelant Prins and Felicis Ventures Partner Aydin Senkut on How to Build a $18B+ Success Story Far Far Away from Silicon Valley
21:34

Hear about Adyen’s journey from a Dutch payments startup to a global public company with more than 15 offices around the world working with large global companies like Facebook, Spotify, Uber and Microsoft. Roelant shares lessons from the company’s own global growth path and will be giving practical tips for companies who are thinking about expanding their business globally. Roelant is joined by Felicis Ventures Founder, Aydin Senkut, who shares the commonalities he sees in successful companies...starting with culture.

Nov 21, 2019
SaaStr 284: Why We Need To Remove The Title of CRO, What Happens If You Apply Customer Success To A Venture Portfolio & Why Net Retention Is The Most Important North Star Metric In SaaS with Travis Bryant, Partner for Founder Experience @ Redpoint Venture
37:36

Travis Bryant is Partner for Founder Experience @ Redpoint Ventures, the venture fund with a portfolio including the likes of Stripe, Netflix, Zuora, Hashicorp and Juniper Networks just to name a few. As for Travis, prior to joining Redpoint, Travis was head of Customer Growth at Front, after spending 5 years building the global Sales organization at Optimizely, the world’s most popular experimentation platform. During his time at Optimizely, the company grew from from $7 to >$90M in ARR and from 40 to 400 people. Before Optimizely, Travis spent 6 years at Salesforce in a number of sales roles including building the first Platform Sales team.

In Today’s Episode We Discuss:

  • How Travis made his way into the world of venture as the first ever Partner for founder experience at Redpoint? What were the 2 biggest lessons Travis took from Salesforce? How transformational is the 12 quarter year for Salesforce?
  • Why does Travis believe we need to abolish the title of CRO? Why does it suggest misalignment between customer and vendor from Day 1? What aspects of CRO’s roles is Travis in favour of? What elements is he not in favour of? What does Travis advise founders when it comes to uniting customer facing teams?   
  • Why does Travis believe that SaaS has upended the economic model but not the engagement model? How does the engagement model with customer need to shift? What does this do to the structure of the conventional funnel? 
  • Why does Travis believe net retention must always be the guiding North Star? How does Travis think about the different steps to customer qualification today and what makes the best SDR’s? What does Travis advise founders when it comes to churn analysis? What questions must you ask? What metrics must you look for? 

Travis’ 60 Second SaaStr:

  1. What motto or quote do Travis frequently revert back to?
  2. What is the most challenging element of Travis’ role with Redpoint?
  3. How should startup operators coming out of larger organisations determine which startup to join? 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Travis Bryant

Nov 18, 2019
SaaStr 283: SocialChorus Co-Founder Nicole Alvino on What I Learned About Corporate Ethics From Enron
18:14

Nicole Alvino, founder of SocialChorus, shares some ‘truth is crazier than fiction stories’ about her time in structured finance at Enron and how she applied what she learned to build a company that has 10 of the Fortune 50 as customers. In your constant effort to grow and win, you’ll get the 5 most important lessons on how to push the envelope just far enough - while keeping your ethics in check.

Nov 14, 2019
SaaStr 282: The Ultimate Guide To Remote Work; All vs Part Remote Teams, How To Maintain Culture Across Teams, Should Compensation Be Location Adjusted, How To Structure Internal Processes with Remote Teams, How Remote Teams Impact Hiring, Sales and Fundr
26:57

Michael Pryor, Co-Founder & CEO @ Trello, now Head of Trello Product with Atlassian following their recent acquisition.

Kolton Andrus is the Founder & CEO @ Gremlin, the failure as a service startup finds weaknesses in your system before they cause problems.

Dylan Serota, Co-Founder and Chief Strategy Officer @ Terminal, the startup that helps you create world-class technical teams through remote operations as a service.

Rachel Carlson, Co-Founder and CEO @ Guild Education, the leader in education benefits offering the single most scalable solution for preparing the workforce of today for the jobs of tomorrow. 

Sid Sijbrandi, Founder & CEO @ Gitlab, a single application for the entire software development lifecycle.

Jeppe Rindom is the Founder & CEO @ Pleo, the simple spending solution for your company automating expense reports and simplifying company expenses.

In Today’s Episode We Discuss:

  • How should founders think about the debate between all remote vs part remote teams? How does life and operations change with each? What are the pros and cons? Is it possible to move between the two overtime?
  • What can one do to maintain culture with remote teams? What processes need to be in place to ensure a cohesive and streamlined communication process? What technical architecture needs to be in place? Where are the breakpoints when it comes to communication? How often does one need to do in person off-sites?
  • How does being remote or part remote impact fundraising? How do VCs think about this new structure of operations? What is the right way to present it? How does being outside a core tech hub impact one’s ability to raise? How should one run a fundraising process if outside a core hub?  
  • How important is it for your team to be near your customers? How does this change according to sector and customer base? How important is it for your team to be near your investors? Does having an exec and sales team in one place and the rest of the team elsewhere work?  

Jason Lemkin

Harry Stebbings

SaaStr

Nov 11, 2019
SaaStr 281: Vista Equity Principal Rene Yang Stewart and Zapproved CEO Monica Enand on From Product Market Fit to Scale
21:24

Rene Yang Stewart, Co-Head and Principal, Vista Equity Partners, and Monica Enand, Founder and CEO, Zapproved discuss growing a company from product market fit to scale. Vista Equity Partners invested in Zapproved in 2017. Hear perspectives from both the investor and founder on growth to scale.

Nov 07, 2019
SaaStr 280: SaaStr CEO Jason Lemkin and Mixmax Head of Revenue Don Erwin on The Secrets to Managing a Successful Sales Team
22:43

How do you manage a sales team when you're at a company with both Free and Freemium Sales-Driven Segments? What about SMB vs. Enterprise Sales? SaaStr CEO Jason Lemkin sits down with Mixmax's Head of Revenue Don Erwin to discuss it all.

Nov 04, 2019
SaaStr 279: Glassdoor CEO Robert Hohman on Building a $1B Marketplace
20:50

Glassdoor CEO Robert Hohman and Battery Ventures' Neeraj Agrawal  walkthrough Glassdoor's $1.2 Billion story from its launch in 2008 to its 2018 acquisition by Recruit Holdings. Hear about the early days of Glassdoor; tactical lessons on scaling—from building a business model and recruiting an all-star management team to advice on building a compelling, innovative company culture; and learn whyGlassdoor’s $1.2 Billion acquisition is just one milestone in the early innings of the company’s story.

Oct 31, 2019
SaaStr 278: Do You Have To Scale From SMB To Enterprise Customers, How To Make The Transition Successfully, What Changes About Customer Acquisition and Support & Why Continuous Customer Development Is The Most Important Thing You Can Do With Krish Subrama
30:28

Krish Subramanian is the Founder & CEO @ Chargebee, the startup that lets you go beyond billing, payments and recurring invoices — to delivering subscription experiences that "wow". To date, Chargebee have “wowed” some of the world’s leading VCs to the tune of $38m including the likes of Insight Venture Partners, Tiger Global, Steadview and Accel Partners. As for Krish, under Krish’s leadership the team has grown to over 300 people and over 5,000 clients making it one of the next generation in truly global SaaS businesses started in India. 

In Today’s Episode We Discuss:

  • How Krish made his way into the world of SaaS and came to found one of India’s fastest growing SaaS companies in Chargebee?
  • What does Krish mean when he says, “in SaaS, you either sell to one of 2 customer profiles”? How does Krish think about purely serving the SMB market? Does one have to move to enterprise? Does one have to expand the product line to retain customers? How does he think about the mortality rate of SMBs?  
  • First, what is continuous customer development? Second, why does Krish believe it is one of the most important things any company must do? What is the process to do it efficiently? Does it have to be in person? What questions reveal the most? How should this data feedback into your product roadmap and pipeline? 
  • How does Krish think your customer acquisition and GTM strategy has to change with the movement from SMB to enterprise? What are the biggest challenges in making this transition? How does your customer success and customer support functions change with the move to enterprise? 

Krish’s 60 Second SaaStr:

  1. Biggest lessons from working with Lee Fixel?
  2. How does one know when is the right time to introduce a new product?
  3. What does Krish know now that he wishes he had known at the beginning?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings 

SaaStr

Krish Subramanian

Oct 28, 2019
SaaStr 277: SaaStr CEO Jason Lemkin and Shopify Plus GM Loren Padleford on Revenue, Ecosystems and The Right Time to Go Upmarket
44:53

When is the right time to go upmarket and how do you serve small, medium and large customers in the same company. SaaStr CEO Jason Lemkin sits down with Shopify Plus GM Loren Padelford to discuss.

Oct 25, 2019
SaaStr 276: Airtable's VP of Customer Engagement Liat Bycel on Why "Hands Off Leadership" Does Not Work, How To Align The Ambitions Of An Individual With The Objectives of The Company & Unpacking The Dilemma of Whether To Go Horizontal Or Vertical When It
31:17

Liat Bycel is VP of Customer Engagement @ Airtable, the startup that works like a spreadsheet but gives you the power to organise anything. To date, Airtable has raised over $170m in funding from some of the best in the business including Thrive, Coatue, Founder Collective, CRV and individuals like Patrick Collison, Ashton Kutcher and Raymond Tonsing to name a few. As for Liat, prior to Airtable, she was the Chief Revenue Officer @ Assist. Before Assist, Liat spent 6 years at Twitter where she first hand saw their hyper-growth, managing a team of 40 across New York and SF and also Liat achieved 102% to quota on average every year. Finally before Twitter, Liat was VP of Sales @ Revolution Prep where she led and managed 7 offices. 

 In Today’s Episode We Discuss:

  • How Liat made her way into the world of SaaS and came to be VP of Customer Engagement at one of Silicon Valley’s hottest startups in Airtable? 
  • What were Liat’s biggest lessons from Twitter on how to hire successfully? What were some of the key takeaways from that experience on how, why and when to fire? Is there ever a right way to do it? How does Liat think about aligning both the personal ambitions of the person with the wider objectives of the company? Why does Liat reject the notion of “hands off leadership?”  
  • Companies often worry about whether to go horizontal or vertical, how does Liat personally think about this choice? What does she advise founders as a result? What are the core questions they should ask to determine their strategy? What are the biggest challenges of having such a vertical product? How does it impact messaging and brand? Product roadmap? Pricing?
  • How does Liat think about challenging the traditional sales model? How does that challenge the structure of the conventional AE and SDR structure? How does Liat think Airtable is pushing up against the traditional customer success model? How has having children impacted how Liat thinks about operating today? What changes with children? 

Liat’s 60 Second SaaStr:

  1. What does Liat know now that she wishes she had known at the beginning of her time with Airtable?
  2. What are Liat’s biggest strengths and weaknesses?
  3. What are the challenges of prioritisation?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Liat Bycel

Oct 21, 2019
SaaStr 275: SaaStr CEO Jason Lemkin and Gainsight CEO Nick Mehta on Founder Struggles from Imposter Syndrome to Vulnerabilites
31:06

SaaStr CEO Jason Lemkin sits down with Gainsight CEO Nick Mehta to discuss what it means to be a SaaS leader. What are the day-to-day struggles? The fears and the worries and what it means to be "crushing it" today.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Oct 17, 2019
SaaStr 274: Messagebird CEO Robert Vis on Scaling To A $60M Series A, Why You Should Not Try To "Scale" & Why You Need To Build Your Business Like A House
29:50

Robert Vis is the Founder & CEO @ MessageBird, the company that allows you to talk to your customers via Voice, SMS and Whatsapp. The company raised a monster $60M Series A from Accel and Atomico with only one prior investor being Y Combinator. As for Robert, prior to MessageBird, he was co-founder and CEO of Zaypay.com which focused on driving mobile payments into 50+ countries, enabling 1.5bln users to pay for virtual goods through their phones (sold to Mobile Interactive Group (MIG). 

In Today’s Episode We Discuss:

  • How Robert made his way into the world of startups and SaaS and came to found Messagebird? What was the a-ha moment for him? 
  • Why does Robert believe the most important element of being a founder is “thinking big”? How as a founder do you balance between thinking big with investors and then the day to day in the weeds with the team? How does Robert as Europe’s mentality of thinking big today? Have our ambitions exceeded what they have been before? How does being in Benelux change how Robert thinks about global ambitions and growth ambitions?  
  • What does Robert mean when he tells founders, “don’t try to scale”? How does Robert think about knowing when a business is ready to scale? Where do many founders go wrong in the preparation for scale phase? What does one need to get in place before scaling?
  • Why did Robert wait 6 years before raising any VC money? Why did he decide then was the right time? Once the raise was in, did he feel the pressure of suddenly having a lot of VC funding? How did his mindset to capital allocation change post-raise? How did he see his decision-making process change post raise? How did raising from the US differ from raising in the UK? 

Robert’s 60 Second SaaStr:

  1. What does Robert know now that he wishes he had known at the beginning of his time with Messagebird?
  2. What keeps Robert up at night? 
  3. What are Robert’s strengths and weaknesses? 
  4. What advice in SaaS does Robert most often hear that he disagrees with?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Robert Vis 

Oct 14, 2019
SaaStr 273: Atlanta Tech Village Founder David Cummings on 7 Lessons Helping Start Pardot, SalesLoft, and Calendly
23:48

David Cummings is the co-founder of the Atlanta Tech Village, Pardot which sold to ExactTarget/Salesforce.com, Hannon Hill,  Rigor, SalesLoft (raised over $75M in capital), Terminus (raised over $25M in capital), and several more. Hear his lessons learned over the years from Pardot to Calendly.

 

Missed the session? Here’s what David talks about:

  • How large a role does funding play?
  • Matching pricing to value
  • How to continuously level up talent

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Oct 10, 2019
SaaStr 272: Asana's Head of Marketing Dave King on How We Are Entering The Third Wave of SaaS Marketing, What That Means For SaaS Marketers and Companies Today & What B2B Marketing Can Learn From B2C
29:07

Dave King is the Head of Marketing at Asana, the work management platform that teams use to stay focused on the goals that grow their business. To date, Asana has raised over $210m from some of the biggest names in tech including Mark Zuckerberg, Peter Thiel, Marc Andreesen, Ben Horowitz, Sean Parker, Ron Conway, Benchmark, Founders Fund and more incredible names. As for Dave, prior to joining Asana, he led the marketing teams at Percolate, Highfive, and Salesforce Community Cloud.

In Today’s Episode We Discuss:

  • How did Dave make his way into the world of SaaS and startups? When did he realise his love of marketing SaaS companies?
  • What does Dave mean when he says, “we are entering the 3rd wave of marketing”? What were the 1st and 2nd chapters? What does the “3rd wave” of marketing mean for marketers today? How does it change what marketing should be focusing on? How does it change how marketing works with sales and customer success? 
  • What does Dave mean when he says, “offsites serve as a crutch for 2 core elements of the marketer's role”? How does Dave advise marketers on crafting their playbook? What are the core questions to ask? Where does Dave see many going wrong here? How does one turn a playbook into a repeatable, measurable process? With channel volatility being so high, is it possible to have a repeatable and predictable process?  
  • What are Dave’s biggest observations on what B2B marketers can learn from B2C? How does that change how Dave thinks about new campaigns and community building with Asana today? Who does Dave think has done this particularly well in the world of enterprise? Are there any challenges to trying to carry over B2C into the world of B2B? 

Dave’s 60 Second SaaStr:

  1. What does Dave know now that he wishes he had known at the beginning of his career in marketing? 
  2. Biggest breakdown in the working of an efficient funnel?
  3. A moment in Dave’s life that has served as an inflection point and changed the way he thinks? 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Dave King

Oct 07, 2019
SaaStr 271: Talkdesk SVP of Client Services Gillian Heltai on How to Build a CSM Team that Generates 130% Net Retention
23:56

Gillian oversees Talkdesk's Customer Success and Technical Support teams, partnering closely with customers to achieve their CX vision. In this session Gillian will walk you through how to build a high performing CSM Team.

 

Missed the session? Here’s what Gillian talks about:

  • How to build a CSM team
  • Avoiding the mistake of over defining the candidate profile
  • How to divide responsibilities across roles

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Oct 03, 2019
SaaStr 270: How To Scale Leader While Retaining Humanity and Personality, Why Starting At SMB Actually Makes Culture Easier & How To Make A Part-Remote Team Your New Superpower
31:28

Jeppe Rindom is the Founder & CEO @ Pleo, the simple spending solution for your company automating expense reports and simplifying company expenses. To date, Jeppe has raised over $78m in funding for Pleo from some European favourites of mine in the form of Creandum and Vaestfonden and then also their most recent round led by Stripes Group in NYC. As for Jeppe, prior to founding Pleo he was the CEO @ Nodes, a design and development house that worked with brands including Loreal, BMW and Lego. Before that, Jeppe was the CFO @ Tradeshift where he first hand saw their scaling to 190 countries with offices in 6 different locations. 

In Today’s Episode We Discuss:

  • How did Jeppe make his way into the world of startups and SaaS with his becoming CFO @ Tradeshift? What were his biggest learnings from Tradeshift and how did that impact his operating mentality? What was that a-ha moment for him with Pleo?
  • Why did Jeppe decide to focus on SMBs from Day 1? How does the product build in the early days differ when building for SMB vs enterprise? Why does Jeppe believe that building for SMB makes it easier to build a great culture internally? How does Jeppe think about when is the right time to move into enterprise? What changes?
  • How does Jeppe respond to 3 common concerns VCs have with SMBs:
  1. The price points are so low that it takes huge volume to scale to meaningful revenue?
  2. The mortality rate of SMBs is so high that you are going to always have high churn due to the customer segment?
  3. Serving SMBs in the way that Pleo does is an intensely competitive space, is this a winner-take-all market? How does Jeppe think about competition? 
  • How does Jeppe think about NPS today? How does Jeppe approach the problem of agency when the buyer is not the user? How does Jeppe think about being customer informed but not customer-driven?
  • Pleo has a part-remote work structure, why does Jeppe advocate for this structure in the face of many saying it either has to be remote or not? What has Pleo done to make it work? What tool stack do they have to ensure seamless communication between remote and non-remote? Where are the challenges? What must one always do?
  • How does leadership change for Jesse in the face of scale? How does Jesse think about scaling humanity and the personal touch with the scaling of his leadership? What are the challenges? When do they start to arise? How has raising in the US compared to raising in Europe? What are the core differences? 

Jeppe’s 60 Second SaaStr:

  1. What does Jeppe know now that he wishes he had known at the beginning?
  2. How did raising from the US differ from raising with European investors?
  3. What would Jeppe most like to change about the world of SaaS today?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Jeppe Rindom

Sep 30, 2019
SaaStr 269: Gorgias CEO Romain Lapeyre on How to Close your First 1000 Customers Based Solely on Data
22:26

Gorgias helps brands automatically respond to basic questions, and track the impact of customer service on sales so support becomes a profit center. Join CEO Romain Lapeyre as he walks you through how to close your first 1000 customers based solely on data.

 

Missed the session? Here’s what Romain talks about:

  • How to build a growth machine
  • How you can tailor onboarding to customers
  • Using data to your advantage

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Sep 26, 2019
SaaStr 268: G2 CMO, Ryan Bonnici on Lessons Learned From Scaling Marketing Team From 5 to 70, The Most Important Role of The CMO Today and How To Create Alignment Between CRO and CMO
40:51

Ryan Bonnici is the CMO @ G2, the company that allows you to get the right software and services for your business with over 897,000 user reviews to help you make smarter buying decisions. As for Ryan, prior to G2 he was Senior Director of Global Marketing at Hubspot where among many other achievements, he scaled HubSpot's marketing-generated sales revenue by 330% year-over-year. Before Hubspot, Ryan was Head of Marketing @ Salesforce (APAC) where he led his team to achieve 227% YoY net-new sales sourced through marketing. Due to his success, Ryan has been named to Forbes’ List of World’s Most Influential CMOs.

In Today’s Episode We Discuss:

  • How Ryan made his way into the world of SaaS from Sydney, Australia and came to be one of the world’s leading CMOs with G2 today? What were Ryan’s biggest takeaways from his time at Salesforce? How did it change his mindset?
  • What are the core differences when comparing marketing functions at the likes of Salesforce to smaller companies like G2? What can they learn from each other? Where does Ryan sit on whether marketing is an art or a science today? How did Ryan turn a $6,000 initiative at Hubspot into a product that generated $64m net revs?
  • What have been Ryan’s biggest lessons in what it takes to acquire the best talent? How does Ryan build candidate pipe? What works most effectively? How does Ryan structure and run the process? What core questions does Ryan ask and find most revealing of the individual’s character? What does Ryan love to see in a candidate? 
  • Does Ryan agree that marketing teams should always be held directly accountable to a number tied to revenue? What type of CMO would Ryan bucket himself as; demand gen or brand? How does Ryan think about the relationship between the two? 

Ryan’s 60 Second SaaStr:

  1. What does Ryan know now that he wishes he had known at the beginning of his career in marketing? 
  2. What is the biggest BS that Ryan often hears in the world of marketing?
  3. Which marketing leader does Ryan most respect and admire and why?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Ryan Bonnici

Sep 23, 2019
SaaStr 267: Menlo Ventures Partner Naomi Ionita on 3 Lessons in Monetization - Matching Price to Value
23:45

SaaS is about creating long-term value for your customer, and being compensated appropriately for that value as a business. Learn actionable monetization tips from a Product/Growth operator turned VC, Menlo Ventures Partner Naomi Ionita.

 

Missed the session? Here’s what Naomi  talks about:

  • How to avoid underpricing your product
  • Fitting your businesses’ product to the market

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Today's sponsor: Traditional customer beta testing can't keep up with the speed of Agile or the demands of continuous delivery. Centercode's approach to real-world Delta Testing fuels product and engineering teams with actionable quality and UX insights before every new release. Visit Centercode.com to learn more.

Sep 19, 2019
SaaStr 266: Zoom CMO Janine Pelosi on Why MQLs and SQLs Are Not Helpful As Labels, How To Create Alignment Between Sales and Marketing & How The Role of CMO Has Changed So Dramatically Over The Years
22:52

Janine Pelosi is the CMO @ Zoom, the next-generation enterprise phone system. Prior to their very successful IPO, Zoom raised funding from some of the best in the business including Sequoia, Emergence Capital, Horizons Ventures and 2 of my favourites in the form of Matt Ocko @ Data Collective and Dan Scheinman. As for Janine before joining Zoom, she spent 11 years at Cisco where among many incredible achievements she led worldwide demand gen for WebEx and led their worldwide digital marketing team with a $25M annual budget. 

In Today’s Episode We Discuss:

  • How Janine made her way into the world of SaaS and came to be one of the leading CMOs today with Zoom?
  • How has the role of the CMO changed over the last 5 years? Would Janine agree with Jason Lemkin that “the role of the CMO is to execute the vision of the CEO”? What makes Janine and Eric’s relationship so successful? What makes Eric the special leader that he is? How does the changing power of the CMO affect their relationship with the CEO?   
  • When is the right time for startups to hire their first CMO? What should they look for in that ideal candidate? What should they have in place in terms of infrastructure, prior to hiring the candidate? What does the right onboarding process look like for a CMO? Where does Janine see many going wrong when hiring their first CMO? 
  • How does Janine look to create alignment between sales and marketing? Why does Janine not believe in having the labels of “MQLs and SQLs”? How does Janine look to reduce the friction when handing off between marketing and sales? What are the common causes? How are we seeing marketing also blend with customer success?

Janine’s 60 Second SaaStr:

  1. What does Janine know now that she wishes she had known at the start of her time at Zoom?
  2. Who does Janine most respect in the world of marketing today? Why?
  3. What would Janine most like to change about the world of SaaS today? 

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Janine Pelosi

Sep 16, 2019
SaaStr 265: WP Engine SVP of Global Sales Matt Schatz on Building a $100M ARR Sales Team - The Second Time Around
24:08

Matt Schatz is SVP of Sales at WPEngine, responsible for defining and executing the global sales strategy. Matt has nearly two decades of senior leadership experience in sales and customer growth, specifically for technology companies with customers around the world including Bazaarvoice, CityVoice and Rackspace.

 

Missed the session? Here’s what Matt  talks about:

  • Getting your “first story”
  • What is a lucky lead and how does that turn into predictable growth
  • Building trust across time zones

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Today's sponsor: Traditional customer beta testing can't keep up with the speed of Agile or the demands of continuous delivery. Centercode's approach to real-world Delta Testing fuels product and engineering teams with actionable quality and UX insights before every new release. Visit Centercode.com to learn more.

Sep 12, 2019
SaaStr 264: Gainsight COO Allison Pickens on Why Customer Success and Product Management Are The New Sales and Marketing, How To Approach Building and Scaling "Services" As A Revenue Line & How To Build A CS Team On A Tight Budget
33:09

Allison Pickens is the COO @ Gainsight, the company that provides everything you need to turn your customers into your biggest growth engine. To date Gainsight have raised over $184m from some of the world’s best VCs in the form of Lightspeed, Bessemer, Insight Venture Partners, Battery Ventures and Salesforce Ventures just to name a few. As for Allison, in her 5 years at Gainsight her list of achievements in endless from running all functions that drive value for Gainsight customers, now a 150 person team, to building out the corporate development function to being the right hand to the CEO. Allison is also an Entrepreneur-In-Residence at Bessemer Venture Partners and sits on the board of RainforestQA. Before Gainsight, Allison started her career in NYC with stints at Bain and The Boston Consulting Group.

In Today’s Episode We Discuss:

  • How Allison made her way into the world of SaaS with Gainsight from her start in finance at Bain in New York?
  • What does a strategic plan really mean to Allison? What is included in it? How should it be structured? In terms of ambition, how does one set ambitious enough plans to be a stretch but not a stretch too far? How does one tie their strategic plan to their financial plan? What is the right way to communicate this throughout the organisation?   
  • Why does Allison believe product marketing and customer success are the new sales and marketing? What have been Allison’s biggest lessons on how to effectively measure adoption? Who is accountable to this number? CS or product management? Does Allison believe that marketing needs to be held accountable to a number directly tied to revenue? 
  • How does Allsion respond to the common negative of “services revenue”? What is an acceptable ratio of services to software revenue? How can one approach setting up a services team for scale? Why is having such a great CS team actually bad for product development in the long run? How can one mitigate this?

Allison’s 60 Second SaaStr:

  1. What does Allison know now that she wishes she had known at the beginning of her time with Gainsight?
  2. How often should CS check in with their customers? What does that look like? 
  3. If on a tight budget, how should one staff a CS team?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Allison Picken

Sep 09, 2019
SaaStr 263: Eventbrite SVP of Platform Pat Poels on Engineering Your Own Luck - The 3 Key Rules of Building Globally Distributed Teams
24:51

Building a company made up of distributed teams presents a plethora of complex challenges that can derail productivity and impact employee retention. But with it comes immense benefits and competitive advantages such as the diversification of ideas, speedier product development, and representation in important regions and time zones. Come and hear about the typical pitfalls (and how to avoid them) from Eventbrite SVP of Platform Pat Poels, an executive with over seven years under his belt leading Eventbrite’s now 300+ strong engineering team that sits across North America, South America, and Europe.

 

Missed the session? Here’s what Pat  talks about:

  • Engineering your own luck
  • How to build an engineering team

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Sep 05, 2019
SaaStr 262: Box's Jon Herstein on How Customer Success Teams Should Structure, Schedule and Execute on Customer Check Ins, Why Delight is Important But Insufficient & Why Customer Success Is Not Responsible For Upsell
36:53

Jon Herstein is the Chief Customer Officer at Box, the company that provides one platform for secure content management, workflow and collaboration. Prior to their IPO, Box had raised funding from some of the best in the business including Andreesen Horowitz, Bessemer, DST, Emergence and Meritech, just to name a few. As for Jon, prior to being Chief Customer Officer at Box, he was Senior VP of Customer Success, responsible for all post-sales services Box provides from implementation to user adoption and more. Before Box, Jon spent 4 years as VP of Professional Services at NetSuite and prior to that, close to 8 years as Senior Director of professional services at Informatica.

In Today’s Episode We Discuss:

  • How did Jon make his way into the world of SaaS and come to be one of the leading figures in the rising tide of the customer success movement?
  • What does Jon mean when he says, “you have to constantly bring your customers to the forefront of your employees minds”? For non-customer facing roles, what can one do to give them that perspective? Does it work to ensure every function spends time in customer support? What is challenging about that? What can be done in the onboarding phase to ensure the individual has the most empathy for the customer, regardless of function?  
  • For those in CS, what is the right communication cadence to check in with their accounts? What should the agenda look like? What outcomes should they drive towards? Should they be involved in the upsell process? How does Jon think about post-mortems on churned clients? How do they structure them? What lost client stands out to Jon and what would he have done differently to retain them?
  • From Jon’s experience seeing Box in hyperscaling, at what stages do SaaS orgs start to break down? Why does Jon think that is? What can be done to proactively try and mitigate this? How does Jon think about the structuring of roles and responsibilities with scale? What does this done well look like? Where do many people go wrong here?  

Jon’s 60 Second SaaStr:

  1. What does Jon know now that he wishes he had known at the beginning of his time with Box?
  2. What motto or quote does Jon frequently revert back to?
  3. What is the most challenging element of Jon’s role with Box today?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Jon Herstein

 

Sep 02, 2019
SaaStr 261: Workday EVP of the Planning Business Unit Tom Bogan on The Top Lessons Learned in Getting to $100M ARR
21:43

Tom Bogan, CEO of Adaptive Insights, a Workday company, will review the key principles to building a successful SaaS company. From team to vision to metrics to funding and more, these principles provide the framework for high-growth, high performing SaaS companies.

How can you develop a winning culture? How can you set aggressive but realistic goals? What’s needed to build the right team in SaaS today?

Missed the session? Here’s what Tom talks about:

  • The important maxims about team building
  • Insights on fundraising and why you might not want to always raise at the highest valuation
  • Personal stories from his time building Adaptive Insights

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Aug 29, 2019
SaaStr 260: HelloSign COO, Whitney Bouck on How Startups Can Attract The Most Seasoned Execs In SaaS, How To Determine Whether A Seasoned Exec Has True Startup Fabric & What Separates Good From Great When It Comes To COOs
40:08

Whitney Bouck is the COO @ HelloSign (now a part of Dropbox). For those that do not know, HelloSign is the company reimagining how you approach your most important business agreements with their award-winning e-Sign solution. As for Whitney, she directly leads the organization's go-to-market efforts, including sales, marketing, business development and customer operations. Whitney is also an advisor to companies funded by the YC Continuity Fund, focusing on enterprise strategy, go-to-market strategy, leadership and execution. If that was not enough, Whitney is also on the board of Ekata, building the global standard in identity verification. Finally, prior to HelloSign Whitney spent close to 5 years at Box where as SVP Global Marketing & GM Enterprise she took on all of marketing globally for Box and was responsible for reshaping the company brand from SMB to enterprise. 

In Today’s Episode We Discuss:

  • How Whitney made her way into the world of SaaS originally with Box and how that led to her coming one of today’s leading COOs with HelloSign? What were Whitney’s biggest takeaways from seeing the hypergrowth of Box? How did that change her operating mentality?
  • What does truly successful exec leadership look like in Whitney’s mind? When is the right time for founders to think about building out their first exec team? What common mistakes do they make in the process? What can founders do to attract seasoned SaaS execs to their early-stage company? What are the questions that suggest an individual has a startup culture to them? What are the indications that they are a “big company” person?  
  • What does Whitney believe is the new role of the CIO? What has changed about their tole and what has driven this change? With their coming front and centre in the org, how does that change both the reporting and operating structure of the business? What are the nuances and intricacies of this role that many do not often consider? 
  • COO is thrown around as a term today, what does it really mean to Whitney? What does Whitney believe separates good from great when it comes to COOs? When is the right time for founders to start looking for their first COO? What should they look for in their first COO? What is the optimal onboarding process for any new COO? 

Whitney’s 60 Second SaaStr:

  1. What does Whitney know now that she wishes she had known at the beginning?
  2. What makes for the optimal relationship between COO and CEO?  
  3. What is the most challenging element of Whitney’s role with HelloSign today?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Whitney Bouck

Ever feel like you can’t really connect with prospects or have an organized workflow to get deals closed? Outreach.io, the leading Sales Engagement platform, supports sales reps and their managers by making it simple to humanize and personalize communication at scale; automating the soul-sucking manual work; and dramatically increasing the productivity and efficiency of all revenue-generating teams. You can check them out at outreach.io/saastr to chat with them and receive a free copy of their new book -- Sales Engagement: How The World's Fastest-Growing Companies are Modernizing Sales Through Humanization at Scale.

 

Aug 26, 2019
SaaStr 259: Pipedrive SVP of Global Sales Tara Bryant on Addressing the Ugly Side of Growth
23:25

Our guest today is Pipedrive SVP of Global Sales Tara Bryant.

Globalization opens up a world of opportunities for sales growth. We often focus on the positive sides of growth—but what about taking a look at the ugly sides? Even what we could consider “good problems” need preparation, and it starts by understanding your team and your goals, including knowing when and how to recruit members of your team, and building in a way that compliments your growth. Do you need more man-power on the customer facing side, or do you need to bring in new management to keep everything in line? Growth isn’t always linear, and the steps to success aren’t always one after the other. How do you prioritize and organize to bring the best possible results? This side of success can be scary, but knowing how to prepare can set you up to reach your companies long term growth goals.

 

Missed the session? Here’s what Tara talks about:

  • What does the ideal candidate look like?
  • How to hire your core staff really well
  • Enabling salespeople to share learnings

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Aug 22, 2019
SaaStr 258: Plaid CEO and Co-Founder Zach Perret on How to Build a Platform that Fuels an Ecosystem
24:31

Companies that have access to more accurate financial data have the ability to develop seamless exchanges of information, providing consumers with improved ways to manage their finances. But how do companies gain secure access to that data in the first place? Enter the platform company. Hear from Plaid co-founder and CEO, Zach Perret and CNBC's Ari Levy as he walks through his lessons learned building Plaid and how it found itself at the center of the fintech ecosystem.

 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Zach Perret

Aug 15, 2019
SaaStr 257: How To Scale Sales Culture Successfully and Sustainably, The Leading Indicators of Burnout and What To Do & The 2 Inflection Points In SaaS Growth Where Things Start To Break with Justin Welsh, Former SVP Sales @ PatientPop
26:01

Justin Welsh is the former SVP Sales @ PatientPop, the startup that offers the first all-in-one practice growth platform that’s HIPAA-compliant and is proven to grow your practice. During his 5 years at PatientPop, Justin grew sales from $0 to $56m alongside the full build-out of the sales team. Before PatientPop, Justin was one of the first 10 employees at ZocDoc, where he spent 4 years in different roles including Director of Strategic Sales. 

In Today’s Episode We Discuss:

  • How Justin made his way into the world of Sales and came to be one of the industry's leading scale up Sales leaders with PatientPop and ZocDoc?
  • How did Justin experience burnout? What were the first indications and signals for him that he was suffering from it? How did it manifest itself in how he carried himself and his behaviour? How did Justin communicate the situation to his bosses? What does Justin advise others in communicating burnout to their superiors?  
  • As a manager observing their team, what are signs that an individual is burning out? What is the right way to approach them to discuss the situation? What options do managers have available to them when faced with a burned out employee? How does micro-management fit into the signals that suggest clear burnout of the individual? 
  • Justin has said before that “culture must precede performance”, what did he mean by this? What actions and communications must they adopt to ensure that this feeling of culture over performance is accepted by the team? With that in mind, how does Justin think about KPI and goal-setting? What can leaders do to create an environment of safety for their team? Where do many leaders go wrong here? 
  • Having seen multiple scaling culture, where do SaaS organisations tend to break down both in terms of culture and process? What are those inflection points? What can be done to actively mitigate these 2 significant points of failure?   

Justin’s 60 Second SaaStr:

  1. What does Justin know now that he wishes he had known when he started at PatientPop?
  2. Sales leader Justin most respects and why?
  3. If Justin could change one thing about the world of SaaS today, what would it be? 

Read the full transcript on our blog. 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Justin Welsh

Ever feel like you can’t really connect with prospects or have an organized workflow to get deals closed? Outreach.io, the leading Sales Engagement platform, supports sales reps and their managers by making it simple to humanize and personalize communication at scale; automating the soul-sucking manual work; and dramatically increasing the productivity and efficiency of all revenue-generating teams. You can check them out at outreach.io/saastr to chat with them and receive a free copy of their new book -- Sales Engagement: How The World's Fastest-Growing Companies are Modernizing Sales Through Humanization at Scale.

Aug 12, 2019
SaaStr 256: Google Cloud VP of Engineering Eyal Manor and Zenoss CMO Megan Lueders
20:24

As a global technology provider powering thousands of SaaS companies, Google is at the forefront of driving exciting and innovative technologies to market. Eyal Manor and Megan Lueders host a fireside chat between Google Cloud and Zenoss, a leader in software-defined IT operations. They discuss the most common and emerging challenges facing SaaS companies today. You’ll also learn how leading SaaS companies are able to scale and thrive in this complex, dynamic environment. Join us for this lively discussion between two innovators.

 

Missed the session? Here’s what Eyal and Megan talks about:

  • How to develop software faster
  • The emergence of new A.I. services
  • Why the “strongest” conversations need to happen between engineering and marketing

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

 

Aug 08, 2019
SaaStr 255: Why Enablement Must Be An Early Investment and How To Structure It, Why The SaaS Incumbents of Today Are Not As Strong As We Think & How To Build A Sales Culture of Confidence Without Arrogance with Vikas Bhambri, SVP Sales and Customer Experi
36:01

Vikas Bhambri is SVP Sales and Customer Experience @ Kustomer, the startup providing Real-time, actionable views of customers with continuous omnichannel conversations and intelligence that automates repetitive, manual tasks. To date they have raised over $113m in financing from some of the best in the business including Tiger Global, Battery Ventures, Boldstart, Canaan, Cisco and Redpoint just to name a few. Prior to Kustomer, Vikas spent over 20 years implementing, consulting, marketing, and selling CRM and ContactCenter solutions with companies like LivePerson and Oracle. 

In Today’s Episode We Discuss:

  • How Vikas made his way into the world of SaaS and came to be at the rocketship that is Kustomer?
  • Why does Vikas believe that a wave of SaaS incumbents are about to be displaced or disrupted? What about the changing tech stacks and infrastructures makes them vulnerable to up and comers? Does this not lead to a consolidatory environment? How does Vikas see the space play out in the coming years when it comes to acquisitions?
  • What have been the dramatic changes that have happened in sales over the last few years? What is the right way for startup founders to address sales rep onboarding? Why is it so crucial to invest in enablement in the early days? How should this enablement be structured? How does this change sales rep payback periods? What is a good payback period? 
  • How does Vikas feel about discounting? If accepted, what must the startup ask for in return? How does Vikas think about multi-year deals? When are they good? What sort of terms make them less beneficial for the vendor? 
  • How does Vikas think about professional services? What is a good margin for professional services? What ratio of revenue is healthy for professional services to account for? When should one look to hire their first customer success reps? What should they look for in those reps? 

Vikas’ 60 Second SaaStr:

  1. What does Vikas know now that he wishes he had known at the beginning?
  2. What is his secret to building diverse teams?
  3. The sales leader Vikas most respects and admirers and why?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Aug 05, 2019
SaaStr 254: HubSpot CEO Brian Halligan on The Funnel is Dead, Long Live the Flywheel.
22:29

The age-old sales funnel has worked fine for decades…until now. Flaws are being exposed, and a new model is imminent. Why is the sales funnel alone no longer an appropriate way thinking about customers? What will emerge to supplement or replace it? HubSpot CEO Brian Halligan and NEA's Hilarie Koplow-McAdams explore the evolution of the marketing and sales funnel you’ve been using for decades to generate traffic and convert and leads into customers.

 

Missed the session? Here’s what Brian talks about:

  • Why a flywheel instead of a funnel?
  • What does the Grateful Dead have to do with Marketing…?
  • What role do T shaped people play?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Brian Halligan

Aug 01, 2019
SaaStr 253: TaskRabbit Founder Leah Busque on Lessons Learned from a Product Reboot
24:23

Leah Busque is currently a General Partner at Fuel Capital, an early stage venture fund located in Silicon Valley. She likes to invest across consumer, B2B saas, and technology infrastructure companies at the earliest stages. In 2008 Leah founded TaskRabbit, the leading on-demand service marketplace in the world. She spent nearly a decade involved with the company as CEO and Executive Chairwoman before she sold the company to IKEA in October of 2017. Hear about her takeaways from a product reboot with TaskRabbit.

 

Missed the session? Here’s what Leah talks about:

  • What are the lessons learned from a product reboot?
  • When  bringing a product to market - what are the BHAGs?
  • How to navigate a product pivot.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Leah Busque

Jul 25, 2019
SaaStr 252: How To Make The Transition From Founder Led Sales To Sales Team, The Truth About Raising a Series A Round As a Non-Bay Area Company and Why Employee 50 Is Such a Big Turning Point
28:21

Eric Christopher is the Founder and CEO @ Zylo, the software management system built for the cloud pioneering a new standard in software management. To date, Eric has raised over $12m for Zylo from some of the best in the business including Byron @ Bessemer, Salesforce, GGV, Semil @ Haystack and the team at High Alpha. Prior to founding Zylo, Eric was the VP of Sales @ Sprout Social leading the revenue operations for over 11,000 customers. Before Sprout Social he was VP of Sales at Shoutlet, responsible for global direct and channel sales teams and developing and managing strategic relationships. Finally, prior to Shoutlet, Eric spent over 7 years at ExactTarget as a Senior Business Development Manager which is where he met High Alpha’s Scott Dorsey. 

In Today’s Episode We Discuss:

  • How Eric made his way into the world of startups and SaaS? What were his biggest takeaways from working with Scott Dorsey @ ExactTarget? What was the founding moment with Zylo?
  • What have been Eric’s biggest lessons when it comes to making the transition from founder led sales to sales team? What would we have done differently with the benefit of hindsight? What were the biggest challenges in the process?  
  • How does Eric think about the importance of quantity vs quality of logos when acquiring your first few customers? Do big logo brand names really provide social validity or is it over-hyped? How does Eric think about discounting in the early days? What can founders do to really extract the most value from the discount they are giving away? 
  • Why does Eric believe that hitting the employee 50 mark is a huge moment for founders and the scaling of the company? What fundamentally changes? What gets harder? What gets easier? How has Eric seen his role evolve with the scaling of the team? How does Eric think about goal and KPI setting with a much larger team? What needs to change? How does one create and retain accountability and ownership at scale?
  • Why does Eric believe that the bar for execution in SaaS in 2019 is so much higher than in 2009? What has changed? How does this make Eric change the way he approaches benchmarking, capital allocation and growth? How did Eric find raising the Series A as a non-Bay area company?

Eric’s 60 Second SaaStr:

  1. What does Eric know now that he wishes he had known at the beginning? 
  2. What is the toughest role to hire for today?
  3. If the money is on the table, take it. Agree or not? Why?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Eric Christopher

Jul 22, 2019
SaaStr 251: Y Combinator Michael Seibel on a Decade of Learnings from Y Combinator
22:40

Michael Seibel is CEO and a partner at Y Combinator and co-founder of two startups – Justin.tv and Socialcam. He has been a partner at Y Combinator since 2013, advised hundreds of startups, and has been active in promoting diversity efforts among startup founders. Hear his take on the future of work with a decade in learnings from YCombinator.

 

Missed the session? Here’s what Michael talks about:

  • How quickly should you hire?
  • When is the right time to sell a startup?
  • How large a differentiator will investors make in your company?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Michael Seibel

Jul 18, 2019
SaaStr 250: Why Enterprise Is Hard Again, Why To Be Successful in SaaS Today You Have To Find The Crumbs Falling From Incumbent Mouths and Why Large Orgs Are So Dysfunctional and How To Poach Talent From Them
34:44

Peter Yared is the Founder & CEO @ InCountry, the startup that allows you to operate globally with data residency as a service meaning they store your mission-critical data in it’s country of origin, without compliance. To date, Peter has raised $8m for InCountry from some of my very favourites including Bloomberg Beta, Felicis, Ray Tonsing @ Caffeinated and CRV just to name a few. Prior to InCountry, Peter founded six and sold 6 enterprise software companies that were acquired by Sun, Citrix, VMware, Oracle, Sprinklr and Prograph. Previously, Peter was also the CTO/CIO of CBS Interactive where he brought CBS into the cloud. At Sun, Peter was the CTO of the Liberty identity consortium that designed SAML 2.

In Today’s Episode We Discuss:

  • How did Peter make his way into the world of enterprise SaaS with the founding and selling of 6 companies and how did InCountry come about? What is that founding moment?
  • Why does Peter feel like it enterprise is really hard again? Why is it no longer to come into large enterprises with a small contract and expand? How does Peter think about enterprise pilots today? Do they really mean anything? What proof points suggest an enterprise is really bought in? What benchmarks should startups bake into the agreements? 
  • How does Peter think about and approach market sizing today? Why is market risk no longer a risk he is willing to take? Where do many entrepreneurs make mistakes when it comes to market timing? In terms of timing, how should entrepreneurs think about whether to start at SMB and move to enterprise or start enterprise and move to SMB? What are the considerations? 
  • Why does Peter believe that large orgs are so dysfunctional today? What can founders do to extract the truly special talent out of these large orgs with big pay packets and troves of options? How has Peter found the transition from CTO to CEO this time? What have been some of the challenges? Where has he asked for external help? 
  • Having built numerous successful remote teams, what have been Peter’s biggest learnings in what it takes to successfully build remote teams? Where do many people go wrong? Does it have to be from Day 1? When is the right time to start thinking about this as a startup?  

Peter’s 60 Second SaaStr:

  1. What would Peter most like to change about the world of Silicon Valley and tech?
  2. Who is the biggest rockstar in the valley that is less well known?
  3. Hire fast, fire fast, agree or disagree? 

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Peter Yared

Jul 15, 2019
SaaStr 249: New Relic CRO Erica Ruliffson-Schultz on Five Critical Steps to Scaling Enterprise
24:35

CRO Erica Ruliffson-Schultz has led New Relic through massive growth, scaling the company’s enterprise business 10x since she joined the business pre-IPO. Growing a company’s revenues, customer base, team, process, and product doesn’t just happen without major work and strategy. Erica will share the five critical steps (and some lessons learned along the way) for scaling in the enterprise.

 

Missed the session? Here’s what Erica talks about:

  • How to change up your marketing mix
  • How to transition from SMB to enterprise
  • Identifying your sweet spot target customers and leveraging your network to access those companies.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Jul 11, 2019
SaaStr 248: What Early Stage SaaS Companies Can Learn Most From Late Stage SaaS Co's, How Marketing Functions Change In SaaS Co's With Scale & Why The Most Powerful Mentorship Is Mentorship From Below with Joe Chernov, VP of Marketing @ Pendo
30:00

Joe Chernov is the VP Marketing @ Pendo, the startup that understands and guides your users allowing you to create products they cannot live without. To date they have raised over $108m in funding from some of the best in SaaS including Meritech, Salesforce, Battery, Spark Capital and Sapphire just to name a few. Prior to Pendo Joe was Chief Marketing Officer at Robin and before that he was the CMO @ InsightSquared where he led the transition from an email-driven leads model to an account-based marketing model. Before InsightSquared, Joe was Head of Content Marketing at Hubspot where he increased blog traffic by more than 1M visits/month and increased leads by 40%. Finally, pre-Hubspot, Joe held VP of Marketing roles at Kinvey and Eloqua.

In Today’s Episode We Discuss:

  • How Joe made his way into the world of startups and SaaS marketing many years ago? Does Joe really believe in the saying that, “no one really knows what they are doing?” Where are the nuances to it?
  • Joe has been CMO and then #2 and alternated between the 2 roles many times, so what the continuous alternating? How does switching from CMO to VP of Marketing prepare you better for each subsequent role? Does Joe agree with the saying that the best in marketing are able to “throw the playbook out of the window”? 
  • What does Joe mean when he says, “the most powerful mentorship is mentorship from below”? What makes the best #2’s just so good? What do they do? What advice would Joe give to a #2 in a role today? What can the individuals do to foster a relationship of deep trust and transparency?
  • Having worked at both early and late stage companies, what does Joe believe the early companies can learn from later stage companies? Does installing very severe ops not reduce the creativity of a young company? What does Joe believe that later stage companies can really learn and take from early-stage companies? 
  • How do the marketing functions differ in both structure and process when comparing early to late stage? What does Joe find to be the biggest challenge within each respective stage? How has Joe seen the content landscape evolve and change radically throughout his career alternating between early and late stage companies?  

Joe’s 60 Second SaaStr:

  1. Who does Joe believe is killing it in SaaS marketing now? Why?
  2. ABM, total BS or real meaning to it?
  3. If Joe could change one thing about SaaS today, what would it be?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Joe Chernov

Jul 08, 2019
SaaStr 247: Hired CEO Mehul Patel on How to Move from Transactional to Recurring Revenue
20:47

Hear from Hired's CEO Mehul Patel on how to move from transactional to recurring revenue. Hired is a marketplace that matches tech talent with innovative companies. Hired combines job matching with unbiased career counseling to help people find a job they love. Through Hired, job candidates and companies have transparency into salary offers, competing opportunities and job details.

 

Missed the session? Here’s what Mehul talks about:

  • How to leverage your company values to drive stability.
  • Hiring people, strategically.
  • Finding your pricing sweet spot.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin
SaaStr
Mehul Patel

Jul 04, 2019
SaaStr 246: Dropbox CCO Yamini Rangan on 5 Myths That Stop SaaS Companies From Moving Upmarket
23:48

Dropbox Chief Customer Officer Yamini Rangan draws on 20 years of experience to challenge five common misconceptions about SaaS success. From beating the competition to over (or under) relying on Outbound, she offers a practical perspective on the frameworks that are holding businesses back from reaching their full potential in a changing landscape.

 

Missed the session? Here’s what Yamini talks about:

  • How to increase the odds of reaching $1B in ARR
  • What is the pull upmarket, why do companies focus their attention there?
  • Common go-to-market myths and lessons.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

 

Jun 27, 2019
SaaStr 245: The Ultimate Guide To ACVs; When and How To Increase Them, Revenue Optimisation Per Lead & What It Means To Truly Be An ARR First Company
26:17

David Skok is a serial entrepreneur turned VC at Matrix Partners. He founded four companies: Skok Systems, Corporate Software Europe, Watermark Software, and SilverStream Software and did one turnaround with Xionics. Three of the companies he founded went public and one was acquired.

Jason Lemkin is the Founder @ SaaStr, the world’s largest SaaS community and leading early-stage SaaS fund with investments in Automile, TalkDesk, Algolia and more.

Jason Vandeboom is the Founder of ActiveCampaign, a sales and marketing automation platform that enables small businesses around the world to meaningfully connect and engage with their customers. Since 2013 with their transition to SaaS have grown to more than $50 million in ARR in less than five years, while maintaining profitability.

Dave Kellogg is a leading technology executive, independent board member, advisor and angel investor. In his most recent role, Dave was the CEO @ Host Analytics where he quintupled ARR, halved customer acquisition costs and increased net retention rates before selling the company to a private equity sponsor.

Fred Shilmover is the CEO and co-founder of InsightSquared, one of Boston’s premiere tech startups paving the way in the sales intelligence space. Throughout the InsightSquared journey, Fred has raised over $25m in VC funding from the likes of DFJ, Bessemer, Salesforce and Atlas Venture.

In Today’s Episode We Discuss:

  • Does David Skok believe that ACV should sit at the top of the metrics stack? What are the 4 metrics that fundamentally matter in your business? What can founders do to their pricing model to extract as much value from each customer? How do the very best businesses structure their pricing for value extraction?
  • If ACV increase is a core focus for our startup, should we hire a sales rep solely selling to enterprise? What are the biggest mistakes founders make in this scenario? What can founders do to optimise revenue per lead? How does on need o approach lead targeting according to the individual skills of their reps?
  • Is it best to start at enterprise and work down to SMB or does SMB and work up to enterprise work best? How does the product have to change with the scaling to enterprise? How does the messaging need to change with the scaling to enterprise? How do you need this change to be reflected in your pricing?    
  • What does it truly mean to be an ARR first company? What is the right way for founders to calculate their differing ACVs? What is the right way to present that when pitching VCs? Where do many founders go wrong in how they present and discuss ACVs with investors?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Harry Stebbings
Jason Lemkin
SaaStr
David Skok
Jason Vandeboom
Dave Kellogg
Fred Shilmover

Jun 24, 2019
SaaStr 244: Flexport CEO Ryan Petersen on How to Build a Truly Global Business from Day One
23:44

Flexport CEO Ryan Petersen will share what he has learned about scaling culture, expanding globally, raising venture capital (or not), and using technology to improve legacy industries.

 

Missed the session? Here’s what Ryan talks about:

  • How Flexport grew to a multibillion-dollar business.
  • How the company broke into the $2T freight forwarding industry.

 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Ryan Petersen

Jun 19, 2019
SaaStr 243: Twilio CMO Sara Varni on The 1 Question That Must Be Top Of Mind For All Marketers, The Truth About Enablement and How It Can Be Used Effectively & The Marketing Playbook, When To Use It vs Throw It Out Of The Window
26:42

Sara Varni is the CMO @ Twilio, the company building the future of communications allowing you to engage customers like never before on voice, SMS, WhatsApp or Video. Prior to their IPO in 2016, Twilio had raised over $250m in VC funding from some of the best in venture including USV, Bessemer, Salesforce and Techstars just to name a few. As for Sara, prior to Twilio she spent 10 years with Salesforce in numerous roles including SVP of Marketing for Salesforce’s Sales Cloud and CMO @ Desk.com, among other roles. If that wasn’t enough, Sara is also an advisor @ Anthos Capital.

In Today’s Episode We Discuss:

  • How did Sara made her way into the world of SaaS and came to be one of the industry’s leading CMOs with Twilio today? What were Sara’s biggest takeaways from her 10 years at Salesforce seeing the incredible hyper-growth first hand?
  • What does Sara mean when she says, “you have to have a creative plan to get your message to market”? Does Sara really believe that there is a playbook when it comes to marketing? How does Sara determine when to throw the playbook out of the window? What resounding question do you always have to ask yourself when thinking messaging?
  • Messaging is very dependent on the customer being targeted, how does the messaging need to be different when targeting SMB vs enterprise? How does the creative plan to get the message to the target customer change dependent on SMB vs enterprise? Where does Sara see most people go wrong here?   
  • Why does Sara so strongly believe in the power of customer stories? What makes the very best customer stories? What would Sara’s advice be to someone who is wanting to start creating them? Where does Sara see so many people go wrong? What are Sara’s tips for creating this alignment between the marketing team that make the stories and the sales team that sell them? Where are there often points of tension?
  • What does the very commonly used term, “enablement”, really mean to Sara? Does it mean you can hire lower quality candidates and upgrade them? How does Sara distinguish between a stretch VP and a stretch too far? What questions does Sara find most revealing in the interview process?  

60 Second SaaStr:

  1. What does Sara know now that she wishes she had known at the beginning?
  2. Who is crushing it in the world of SaaS marketing today?
  3. What is the most common reason for the breakdown of an efficient funnel?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Sara Varni

Jun 17, 2019
SaaStr 242: Namely CEO Elisa Steele on How to Win the Talent War
18:53

It’s the employees’ market. There are more jobs than there are qualified people to do them. SaaS companies face sustained headwinds in the attracting, cultivating, driving productivity, and retaining talent. Your market competitors are your adversaries, but so is the entrepreneur sitting right next to you whose business is in a completely different sector. Namely CEO Elisa Steele shares practical advice on how to win three key Talentshare battles, which are essential to winning the Marketshare war.

Missed the session? Here’s what Elisa talks about:

  • How to win Talentshare when the system is stacked against you.
  • How to drive synchronization, productivity when your needs are constantly evolving and the talent mix is incredibly fluid and diverse.
  • How to use Culture as the lever to maximize the ROI that you get out of the biggest investment your business will ever make.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Elisa Steele

Jun 13, 2019
SaaStr 241: Dave Kellogg on The BIggest Takeaways From Being In The Room For Sequoia’s “RIP Good Times”, Why Founders Should Raise As Much As Possible But Spend According To Plan & The Right Way To Think About Effective Quota Construction
34:23

Dave Kellogg is a leading technology executive, independent board member, advisor and angel investor. In his most recent role, Dave was the CEO @ Host Analytics where he quintupled ARR, halved customer acquisition costs and increased net retention rates before selling the company to a private equity sponsor. Before that Dave was SVP/GM of Service Cloud @ Salesforce where he led the $500m line of business for customer service applications. Finally pre-Salesforce, Dave was CEO @ MarkLogic where he grew the team from 40 to 240 and revenues from $0 to an $80m revenue run rate. If that was not enough, Dave currently or has previously sat on the boards of Nuxeo, Alation, Aster Data and Granular.

In Today’s Episode We Discuss:

  • How did Dave make his way into the world of SaaS over 20 years ago? How did seeing the boom and bust of the dot com and 2008 affect Dave’s operating mentality?
  • What were his biggest lessons from being in the Sequoia boardroom when they presented “RIP good time”? How does Dave think about when is the right time to raise? How does Dave advise founders on how much is the right amount to raise? Does Dave agree that if the money is on the table founding teams should take it? Why does Dave believe 99% of companies die?
  • The first step in being acquired by a PE house is “making the book”, what goes into “making the book”? Who is involved? How long does it take? What are the clear differences between a good book and a bad book? How should execs think about making exciting enough go-forward plans for it to be attractive to buyers but also realistic enough that they can hit it in the acquisition process?  
  • How does the selection for who receives the book look? Who decides this? What is the fundamental aim in the distribution of the book to many parties at the same time? What does Dave know now about the world of PE that he wishes he had known at the beginning? IOI’s is the next step, what are they? How do they set up the process from there?
  • How do management meetings with potential PE acquiring firms compare to founders meeting VCs in the early days? How many meetings is normal to have in this process? How long do they last? What does Dave believe is crucial to achieve in these in person meetings? How much of a role does price play in selecting the ultimate acquiror? How much of a role does their brand and reputation play?

60 Second SaaStr:

  1. What does Dave know about the process that he wishes he had known at the beginning?
  2. The biggest misconception about the world of PE and acquisitions?
  3. Burn rate is a function of the personality of the CEO? Agree or disagree? Why?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Dave Kellogg

Jun 10, 2019
SaaStr 240: SaaStr 240: Brex Founder and CEO Henrique Dubugras on Lessons From a Second-Time Founder: How Brex Went From 0 - $1B in Under 2 Years
21:28

Brex Co-Founder and CEO Henrique Dubugras will talk about what he's learned building the fastest-growing B2B company. Henrique started his first company at 16 and has now built two successful companies from nothing. Learn what he did differently the second time around and the specific decisions he made to drive growth among B2B companies with Brex.

 

Missed the session? Here’s what Henrique talks about:

  • How Brex grew from a few basic functionalities to a corporation
  • Growing from $0 to $2B in ARR in less than two years.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Henrique Dubugras

Jun 06, 2019
SaaStr 239: How To Raise Prices and Still Leave Money On The Table, How To Analyse The Pros and Cons of Monthly vs Annual Deals & The Leading Indicators That Your Sales Machine Is Working with Amit Bendov, Founder & CEO @ Gong.io
31:14

Amit Bendov is the Founder and CEO @ Gong.io, the startup that provides you with powerful visibility into your customer conversations with conversation intelligence. To date, Amit has raised $68m in funding for Gong from the likes of Norwest, Battery Ventures, Cisco Investments and Wing Venture Capital just to name a few. As for Amit, prior to founding Gong, Amit was the CEO @ SiSense BI software that enables business users to connect to multiple databases of any size. Before that Amit was the CMO @ Panaya, helping companies that use SAP or Oracle to reduce 80% of their ERP upgrade. Finally before that Amit was the Founder & CEO @ SparkThis, an outsourced marketing and sales service for cloud companies.

In Today’s Episode We Discuss:

  • How Amit made his way into the world of SaaS and came to found Gong, the leader in conversational intelligence driving deal conversion and rep success?
  • How does Amit approach the process of idea validation? What can founders do to make sure their idea is a hit before they start work on it? How many customer conversations should they have? What questions are crucial to ask? What are the answers they want to hear? What is enough proof that there is a ready and willing customer base for this idea?  
  • With many products starting as free, how does Amit think about when is the right time to start charging for your product? What does Amit think about the differing variable price mechanisms that one can choose? How does one have a variable pricing mechanism without disincentivizing users to use the product? What does Amit advise founders should charge in the early days? Should they leave money on the table?
  • How does Amit think about monthly/vs annual deals? What are the core benefits and drawbacks of each? How important is it that multi-year deals are paid upfront? What must you account for with regards to multi-year deals? How do you know when you have the right pricing mechanism in place from the sales cycles of the reps?

60 Second SaaStr:

  1. What does Amit know now that he wishes he had known in the beginning?
  2. The hardest role to hire for today?
  3. The hardest element of Amit’s role as CEO of Gong?
  4. SDR is the most important function in the sales org, agree or not and why?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Amit Bendov

Jun 03, 2019
SaaStr 238: Salesforce Mobile EVP Leyla Seka and Sr. Director of Global Equality Programs Molly Ford on How They Did It: Gender Equality, Equal Pay and Racial Equality
20:16

Join Molly Ford, Salesforce Global Equality Programs Senior Director, and Leyla Seka, Salesforce VP of Mobile for actionable advice they have applied on their own journey. Here are their lessons learned on driving change in gender equality, equal pay and racial equality within Salesforce.

Missed the session? Here’s what Molly and Leyla talk about:

  • Building a community of allies and allyship
  • How to drive equality
  • What you can be doing as an employee to help drive the culture you want

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Molly Ford

Leyla Seka

 

May 30, 2019
SaaStr 237: Rippling's Parker Conrad on How To Clear The Bar of "Not Another System" Thinking in SaaS, Why Your Engineers Should Be Doing Support For As Long As Possible & Why Remote Teams Is The Worst Way To Build A Company, Apart From Every Other Way
31:57

Parker Conrad is the Founder & CEO @ Rippling, the startup that gives you back your time from payroll to employee computers, Rippling makes it unbelievably easy to manage your company’s HR and IT - in one system. To date Parker has raised over $59m in funding from some of the best in the business including Mamoon @ Kleiner Perkins, Garry Tan @ Initialized, Justin Kan, SV Angel and Y Combinator, just to name a few. As for Parker, prior to founding Rippling, he was the Founder & CEO @ Zenefits, the startup he built from $0 to $60m in ARR in just 3 years. Before that he co-founded Sigfig where he grew assets on the platform to over $35Bn across 500k users.

In Today’s Episode We Discuss:

  • How Parker made his way into the world of startups and SaaS, came to found Zenefits and what was that a-ha moment for the founding of his most recent company, Rippling?
  • What does Parker do with regards to operational scaling that is unconventional but works? Why does Parker believe it is fundamentally better to wait for as long as possible before hiring customer support? Why should engineers also be doing customer support?  
  • Why should your engineers be heavily involved in the customer support hiring process? What are the benefits of this? How can one prevent their customer support team from being a wall of protection for the product and eng team? How can you ensure seamless collaboration and communication flow between product and customer support?
  • Stripe last week recently announced their 5th office would be… “remote”, so how does Parker feel about the building of remote teams? What are the most important things when establishing your first remote team? What do you look for in those hires? What can be done to ensure a greater feeling of community and closeness despite the distance? What have been some of the biggest challenges for Parker in building out the remote team?
  • Parker has been a CEO with 3 different companies now and so how has he seen his style and approach change over the years? What has Parker found the hardest to get good at? When advising founders on fundraising, what advice does he give? How can founders know when is the right time to raise? How should they look to build relationships with investors between raises?

60 Second SaaStr:

  1. What does Parker know now that he wishes he had known in the beginning?
  2. What one thing would Parker like to change about tech and Silicon Valley?
  3. Biggest mentor and what has Parker learned from them?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Parker Conrad

May 27, 2019
SaaStr 236: Logikcull CEO Andy Wilson on $0 to $10M in 19 Months: The How, When & Why + 10 Mistakes Along the Way
22:56

Join Logikcull's CEO and Co-Founder Andy Wilson as he takes you through the mistakes made going from $0 to $10M in 19 months.

 

Missed the session? Here’s what Andy talks about:

  • Selling the way your customers want to buy.
  • What you need to know about hiring, firing, advisors, and culture
  • Why SaaS is your business model, not your mission.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Andy Wilson

May 23, 2019
SaaStr 235: Scaling To 3,000+ Customers Without A Single Sales Rep, The Most Important Trait To Look For In Your First Sales Hire & How To Make Your Customers Your Best Investors with Andrew Filev, Founder and CEO @ Wrike
29:24

Andrew Filev is the Founder & CEO @ Wrike, the cloud based collaboration and project management software that scales across teams in any business. In Dec 2008, Vista Equity Partners acquired a majority stake in Wrike for a deal reportedly valuing the company at $800m. Before this transaction, Andrew had raised over $45m in funding from the likes of Rory @ Scale and Bain Capital Ventures just to name a few. As for Andrew, he started his first software development company at the age of 18 and has been running Wrike for the last 13 years alongside advisory roles with both Ditto and Appulate.  

In Today’s Episode We Discuss:

  • How Andrew made his way into the world of SaaS from his starting his first software business at the age of just 18 and how that led to his founding of Wrike?
  • How does Andrew advise founders on the question of whether to start in enterprise or SMB? What are the benefits of starting in SMB? How does the founder know when is the right time to start moving to enterprise? What are those leading indicators? How does the product and what you invest in proactively need to change as you move into enterprise?     
  • Andrew has been the CEO for the last 13 years, how has the role of CEO changed over those years? What has been the most challenging phase? If the CEO is the guardian of the culture, what does a great guardian look like? What 3 elements does Andrew focus almost exclusively on today within his role as CEO?    
  • What does Andrew think are the major breaking points in the scaling of companies? Where does culture begin to breakdown? What can be done to mitigate this? How does Andrew think about using employee satisfaction surveys internally? How can one accurately determine the strength of your manager set?

Andrew’s 60 Second SaaStr:

  1. What does Andrew know now that he wishes he had known at the beginning?
  2. No man’s land in SaaS pricing, does it exist?
  3. Sales rep productivity, what is good to Andrew?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Andrew Filev

May 20, 2019
SaaStr 234: PagerDuty CEO Jennifer Tejada and Duo Security CEO Dug Song on The Top Things No One Really Tells You About Scaling
24:49

Duo Security Co-Founder and CEO Dug Song and PagerDuty CEO Jennifer Tejada discuss building, enabling, and leading great teams through 10K+ customers, $100M+ ARR, $1B+ valuation and beyond - all while earning 4.5+ Glassdoor company ratings and 98%+ CEO approvals from 500+ total employees!

 

Duo Security is a cloud-based provider of unified access security and multifactor authentication was acquired by Cisco for $2.35 billion in October 2018. PagerDuty is a leading digital operations management platform for organizations announced new financing in September 2018 at a $1.3 billion valuation.

 

Missed the session? Here’s what Jennifer and Dug talk about:

  • When is the right time to raise money?
  • How can you better manage the board?
  • Should you worry about competitors?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Jennifer Tejada

Dug Song

May 16, 2019
SaaStr 233: G2 Founder & CEO, Godard Abel on How To Set Ambitious But Achievable Sales Rep Quotas & The Lessons From 2 Successful Exits on The Breaking Points In The Scaling of SaaS Orgs
29:30

Godard Abel is the Founder & CEO @ G2, the company helping millions of business make better product buying decisions every month. To date, Godard has raised over $100m in funding with G2 from the likes of Accel, IVP, High Alpha, Pritzker Group and Chicago Ventures just to name a few. As for Godard, he founded his first business, BigMachines, in 2000, a business he scaled to $50m in revenue and over 300 people up until it’s acquisition to Oracle 11 years later for $400m. Godard then became CEO @ Steelbrick where he took them from 5 to 200 employees and increased bookings by 37x in 7 quarters. Steelbrick was ultimately acquired by Salesforce where he spent a year and a half before starting G2.  

In Today’s Episode We Discuss:

  • How did Godard make his way into the world of SaaS over 20 years ago? What was the a-ha moment for the founding of G2 for Godard?
  • Having been a Founder through the bust of 2000, how did seeing that macro environment impact his operating mentality today? What did it teach him about capital efficiency and investing ahead of time? Taking the team from 70 to 20, what were his lessons on the right way to let someone go? Where do many people get it wrong today?     
  • Why does Godard advocate for working with people that you have worked with before? How can you find the zone of genius for the people that you work with? How does Godard set a culture of ambition and determination around goals but also prevent dejection if the goals are not hit? How often should rep quota be hit? Why is that the right ratio?    
  • Where does Godard believe that things really start to break down in the scaling of an organisation? What can you do to get ahead of those moments and minimise their impact? How many direct reports does Godard believe is the optimal and then the maximum for a manager to have? How have his thoughts on this changed over time?

Godard’s 60 Second SaaStr:

  1. What would Godard like to change in the world of SaaS today?
  2. What does Godard know now that he wishes he had known at the beginning?
  3. If an investor can provide one value, what would it be and why?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

 

Jason Lemkin

Harry Stebbings

SaaStr

Godard Abel

 

May 13, 2019
SaaStr 232: Fmr. Host Analytics CEO Dave Kellogg on The Top 5 Questions Every CEO Wrestles With
21:16

Dave Kellogg is CEO of Host Analytics and prolific blogger. Join him as he takes you through lessons learned from Host Analytics on the top questions every SaaS CEO wrestles with. Dave was CEO of Host Analytics from 2012 to 2018 where he quintupled ARR while halving customer acquisition costs in a highly competitive market, ultimately selling the company in a private equity transaction.

 

Missed the session? Here’s what Dave talks about:

  • When is the right time to raise money?
  • How can you better manage the board?
  • Should you worry about competitors?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Dave Kellogg

May 09, 2019
SaaStr 231: Why SQLs and MQLs Are Redundant, Why You Have To Eliminate Hand Offs Between Go-To-Market Teams & Why One North Star For The Whole Company Can Be Damaging with Jason Reichl, Founder & CEO @ GoNimbly
26:54

Jason Reichl is the Founder & CEO @ GoNimbly, the first SaaS consultancy to focus on revenue operations. Currently growing 100% year over year, working with companies to un-silo their operations and create one strategic revenue ops team to support their Go To Market strategy. In the past, Go Nimbly has helped companies like Zendesk, Twilio, PagerDuty and Coursera to achieve alignment and increase revenue by 26%. As for Jason, prior to co-founding GoNimbly, he was Director of Product Management @ TradeShift and before that was VP of Product Management @ Lanetix.  

In Today’s Episode We Discuss:

  • How Jason made his way from Director of Product Management at Tradeshift to changing the way we think about scaling revenue operations with GoNimbly?
  • Why does Jason believe that we have to remote handoffs between go to market teams? Why are they so damaging? How does Jason believe SaaS companies can use a “swarming” effect to create the best buyer experience for their customer? What does this involve? How does this change the type of metrics that we track?
  • Why does Jason believe that your North Star has to be revenue in the go to market teams? Why does Jason also believe that it is damaging to have the same North Star across the entire company? How should North Star’s be segregated between GTM teams and biz ops teams? What are the mistakes many companies make when setting their internal North Stars?
  • Why does Jason believe that alignment is a dirty word? Why is alignment actually a negative for the customer experience? What does Jason view as vanity metrics? If one has vanity metrics in place, what does Jason recommend as to keeping them or phasing them out?

60 Second SaaStr:

  1. What does Jason know now that he wishes he had known in the beginning?
  2. How does Jason feel about multi-year deals?
  3. How does Jason feel about channel/partner sellers?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

May 06, 2019
SaaStr 230: SaaStr 230: AWS VP Sandy Carter on Customer Success at Scale
22:33

We live in a Shark Tank world: competition is fierce, talent is better than ever, and we’re all striving to come out on top. CEOs everywhere are seeking to innovate, but 81% say their teams are not equipped to meet the challenges needed to compete in today’s marketplace.

 

Innovation is about empathy with your customers. It's all about customer obsession! In this session, Sandy Carter, AWS Vice President will hone your superpower - not of customer focus, or customer driven, but customer obsessed.

 

 

Missed the session? Here’s what Sandy talks about:

  • How to start with success and think backwards
  • Think about how to present a feature or product before you start building.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Sandy Carter

May 02, 2019
SaaStr 229: The 2 Most Important Numbers For Your SaaS Business, Why You Should Not Have VPs Until $5m in Revenue & How To Manage Top Of Funnel Efficiently But Aggressively with Manny Medina, Founder & CEO @ Outreach
27:29

Manny Medina is the Founder & CEO @ Outreach, the market leading sales engagement platform that turns your team into a revenue driving machine. To date, Manny has raised over $114m in funding from some great people including friends of the show in the form of Alex Clayton @ Spark, Mayfield, Trinity Ventures and DFJ Growth, just to name a few. Prior to founding Outreach, Manny spent 7 years with Microsoft where he ran the Latin America and Canada business development group for Microsoft’s emerging mobile division, representing $50M of yearly revenue. Befofe that Manny was a Senior Product Manager @ Amazon where he engineered the compensation system for Amazon Associates and Web-Services which accounts for 15% of Amazon's traffic.

In Today’s Episode We Discuss:

  • How Manny made his way to found the leader in sales engagement from product management at Amazon and Business Development @ Microsoft?
  • How does Manny fundamentally approach managing top of funnel? What are the 2 big dangers of not managing it aggressively? What can be done to ensure not only full but high quality top of funnel?
  • Why does Manny believe it is so important to track pipeline coverage as one of your core metrics? What does good look like when it comes to pipeline coverage? How does this change if you are creating vs in an existing market? How does Manny think about specialisation within the sales function? Why are SDR’s 99% of the time not able to carry leads to completion?
  • How does Manny think about quota construction today? Does Manny err on the side of setting high to be ambitious or setting low to increase confidence? How can managers really empower their reps to be aggressive in hitting their quota and exceeding it? How does Manny think about resource allocation on the individual rep level? What is sufficient? What is excessive?
  • Does Manny believe that the founder should always be responsible for selling their product at one moment in time? How did Manny sell the first $1m in ARR simply through walking the streets of SOMA and selling door-to-door? What were his biggest lessons from doing this?  Why does Manny believe that you should not have a VP before $5m?

60 Second SaaStr:

  1. What does Manny know now that he wishes he had known in the beginning?
  2. What does the future of sales prospecting look like to Manny?
  3. What would Manny like to change about the world of SaaS today?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Manny Medina

Apr 29, 2019
SaaStr 228: Twilio CEO Jeff Lawson and Glitch CEO Anil Dash on the Secrets to Building a Billion in ARR and Being an Ethical leader.
24:34

Join Glitch CEO Anil Dash and Twilio CEO Jeff Lawson for a discussion about the ethical implications of technology in today’s society. Jeff and Anil discuss how social media and AI are changing the way we think about the impact of technology on society as well as the responsibility of tech leaders for this impact.

 

Missed the session? Here’s what Jeff talks about:

  • How taking no stance as a business leader today, is taking a stance
  • How to set concrete numbers for diversity goals
  • The impact of corporate culture on employee happiness

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Jeff Lawson

Anil Dash

 

 

 

Apr 25, 2019
SaaStr 227: Why Deal Size In The Early Days Does Not Matter, Why TAM In The Traditional Sense Barely Matters & Why You Have To Invest In Customer Success Before You Think You Need It with Alexandr Wang, Founder & CEO @ Scale
27:03

Alexandr Wang is the Founder & CEO @ Scale, the startup providing high quality training and validation data for AI applications. To date, Alexandr has raised over $23m with Scale from some of the best in the business including Index, Accel, Y Combinator, Dropbox’s Drew Houston, Justin Kan, Thumbtack’s Jonathan Swanson and more. Prior to founding Scale, Alexandr was a Tech Lead at Quora, directly responsible for all speed projects and before that a software engineer at Addepar responsible for building and maintaining financial models.

In Today’s Episode We Discuss:

  • How did Alex make his way into the world of SaaS and come to found Scale? What were some of his biggest takeaways from seeing the first hand scaling of Quora and Addepar?
  • Why does Alex take the contrarian view that “TAM in the traditional sense barely matter”? What two characteristics of the market should founders really look to examine? How does Alex approach the element of market sizing? Does he prefer top down or bottoms up and why?
  • Why does Alex believe that you must invest in customer success before you think you need it? What were the benefits for Alex of investing early in customer success? Why does CS over sales ultimately drive the growth of your company? How does one know when is the right time to hire their first in customer success? What is the ideal profile of this candidate?
  • How does Alex think about the integration of customer success and product teams? Why is it crucial from the product perspective that founders pick their first customers well? How can your customers drive your product decisions? How can one ensure to be customer informed and not customer driven?     
  • Why does Alex believe that in the early days it is not important to focus on the size of the deals you are signing? What should founders be focusing on with these early customers instead? When is the right time to flip the switch and opt for value extraction as a more primary objective? How does Alex respond to the fact that VCs often look at these first customer deals as an indication of the size of the pain point you are solving?  

60 Second SaaStr:

  1. What does Alex know now that he wishes he had known in the beginning?
  2. What does Alex believe is the hardest role to hire for today?
  3. Who does Alex think is crushing it in the world of SaaS today?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Alexandr Wang

Apr 22, 2019
SaaStr 226: Survey Monkey CMO Leela Srinivasan on 7 Tips For Using Customer Feedback To Build Rabid Fans and Make More Money
22:53

Leela Srinivasan is the CMO of SurveyMonkey. Join her as she takes you through her seven tips for using customer feedback and building rabid fans. Consistently ramping your ARR is a whole lot harder if your customers don’t stick around. In an age where earning customer loyalty and trust is harder than ever, the road to lifetime value is paved with customer feedback. If you take the time to listen, understand and act on what your customers are thinking and feeling, you’ll create an army of advocates and drive topline revenue growth for good measure.

 

Missed the session? Here’s what Leela talks about:

  • How to create an army of advocates
  • How to drive topline revenue growth
  • Real world examples from businesses that are listening and acting on customer feedback every day.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Leela Srinivasan

 

Apr 18, 2019
SaaStr 225: Biggest Lessons From The AppDynamics and GlassDoor Scaling, 3 Elements Marketing Team Comp Has To Be Tied To & How To Create True Alignment Between Marketing and Sales with Stephen Burton, VP of Smarketing at Harness.io
28:53

Stephen Burton is VP of Smarketing at Harness, the industry’s first continuous delivery as a service platform. To date, Harness has raised $20m in funding from the wonderful Matt Murphy @ Menlo Ventures and BIG Labs. Prior to Harness, Stephen was VP of Marketing at Glassdoor, managing a team of 52 in product marketing, helping grow B2B revenue from $19m to $90m in just 2 years, leading to their $1.2Bn acquisition. Before Glassdoor, Stephen was VP of Product Marketing at AppDynamics where he helped grow B2B revenue from $0 to $100m in a staggering 3 year period, resulting in their $3.9Bn acquisition by Cisco.

In Today’s Episode We Discuss:

  • How Steve made his way into the world of SaaS and came to be VP of marketing at 2 of the larger B2B exits of the last decade in AppDynamics and Glassdoor? What were Steve’s biggest takeaways from seeing the hyper-scaling at AppDynamics?
  • Steve has previously said, “sales and marketing must be one team”. Why does he believe this is so important? What can leaders do to turn this into reality? What works? Where has Steve seen many make mistakes? Where does Steve find common points of tension between sales and marketing? WHat are the 3 elements that marketing comp should be tied and aligned to?
  • What does Steve mean when he says, “marketers need to embrace the developer first mindset”? What does this mean for the processes used by marketing teams? Speaking of developer-first, how can startups compete in a war for talent against FB and Google? How can they integrate autonomy into their hiring process as a core advantage?     
  • For Steve, what does devops really mean? What does Steve believe is the right culture for devops teams? Does it differ from traditional dev teams? How can a CEO determine when is the right time to fundamentally invest in devops? What are the required steps to make devops teams as successful as possible?

60 Second SaaStr:

  1. What does Steve know now that she wishes she had known at the beginning?
  2. When is the right time to pour fuel on the company fire?
  3. The playbook? Is there one? Dangers? Copyability?
  4. What would Steve most like to change in the world of SaaS?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Stephen Burton

 

Apr 15, 2019
SaaStr 224: Zendesk CEO Mikkel Svane on Lessons from Zendesk Beyond $1B ARR
21:30

Mikkel Svane is the CEO of Zendesk and author of "Startupland". Join him as he takes you through his lessons taking Zendesk beyond a billion in ARR. Mikkel founded Zendesk in Copenhagen, Denmark in 2007 before moving the company to San Francisco in 2009.

Missed the session? Here’s what Mikkel talks about:

  • The future of the cloud
  • The rise of the public cloud and re-platforming of the tech stack
  • How business applications are sold and delivered leveraging SaaS

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Mikkel Svane

Apr 11, 2019
SaaStr 223: Intercom COO Karen Peacock on Scaling from $1MM to $500MM ARR: 5 Strategies to Drive Your Next Wave of Growth with Intercom
22:49

Karen Peacock is COO of Intercom, one of the fastest growing SaaS businesses of all time. She has led businesses of all sizes through massive growth.  Listen to her top 5 lessons learned building and scaling SaaS businesses from $1M to $500M in ARR including expanding to serve upmarket customers, moving from product to platform, and hiring to drive breakthrough customer experiences and business growth.

Missed the session? Here’s what Karen talks about:

  • How should you expand your market?
  • How to move upmarket
  • The steps to building a product and creating an end to end experience

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Karen Peacock

Apr 04, 2019
SaaStr 222: Flexport CRO Ben Braverman on Why It Is Total Horseshit That The Best Sellers Don't Make Good Managers, Why Specialisation Does Not Lead To The Best Customer Experience & Scaling Revenue From $18k MRR in 2014 to a $472m Year In 2018
39:00

Ben Braverman is the CRO @ Flexport, one of the world’s fastest growing startups combining technology, infrastructure and expertise, to build the operating system for global trade. To date they have $1.35Bn in funding from some of the biggest and best in the business including Softbank’s Vision Fund, Founders Fund, DST, Susa Ventures and Y Combinator, just to name a few. As for Ben, he spearheads global sales and go to market teams. Prior to Flexport, Ben helped drive two high-growth companies to successful acquisitions: URX (acquired by Pinterest) and Heyzap (acquired by Fyber).

In Today’s Episode We Discuss:

  • How Ben made his way into the world of startups and came to be CRO of one of the world’s fastest growing startups in the form of Flexport?
  • Why does Ben fundamentally disagree with the specialisation of roles within SaaS companies? What does he believes this does to the customer journey and relationship? How should one thing about role segmentation and allocation of accounts with this in mind? Where does Ben see many people going wrong here?
  • Why does Ben believe it is “total horseshit to say the best sellers don’t make the best managers”? What must founders try and figure out before hiring their sales leader? What are the leading indicators that suggest a sales rep has the ability to be a sales manager? How does Ben determine between a stretch VP and a stretch too far?   
  • What does Ben mean when he says, “there are 3 distinct buckets of sales management”? What are they and what is their relationship between one another? Why does Ben believe one does not need sales management in the early days? What is the best way to train reps and determine payback period fast? Why does Ben believe sales ops is the most underappreciated role in the valley?

60 Second SaaStr:

  1. What does Ben know now that he wishes she had known at the beginning?
  2. What is the optimal relationship between CRO and CEO?
  3. What does Ben believe in SaaS that most around his disbelieve?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Ben Braverman

Apr 03, 2019
SaaStr 221: HBS Sr. Lecturer and Former Hubspot CRO Mark Roberge on His Step by Step Guide to Revenue Growth
30:00

Mark Roberge is a senior lecturer with Harvard Business School, former CRO of Hubspot and author of the bestseller "The Sales Acceleration Formula". Join him as he takes you through his step by step guide to revenue growth.

 

Missed the session? Here’s what Mark talks about:

  • An in-depth guide to driving revenue growth by company stage
  • When to scale and how fast
  • Product market fit, go-to market fit during the experiment stages

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Mark Roberge

Mar 28, 2019
SaaStr 220: Salesforce Mobile's EVP, Leyla Seka on Her Biggest Lessons Seeing Salesforce Scale From $500m to $16Bn, What Needs To Be In Place For Hyper-Scale & How Leaders Build Trust In Their Organisation
33:37

Leyla Seka is the executive vice president of the Salesforce Mobile platform experience. Over Leyla’s incredible 11 year journey with Salesforce she has seen the team scale from 1,800 to over 40,000 and revenue scale from $500m to over $16Bn. In Leyla’s role today, she leads the charge on extending the power of Salesforce with a full portfolio of mobile apps, and is responsible for driving product, go-to-market and other key programs around Salesforce’s mobile offerings. Prior to her current role, Leyla was executive vice president of the Salesforce AppExchange, where she launched a refreshed AppExchange storefront, a new partner program, and built an entire AppExchange-focused team, resulting in more than 4,000 solutions, installed nearly 6 million times. Beyond her day-to-day role, Leyla is also the executive sponsor of BOLDforce, Salesforce’s organization for expanding and empowering the black community at Salesforce.

In Today’s Episode We Discuss:

  • How Leyla made her way into the world of SaaS with Salesforce when it had 1,800 people and $500m in revenue?
  • What were Leyla’s biggest learnings on people and business model through seeing the first hand hyper-scaling of Salesforce from $500m to $16Bn? How did Leyla evolve and scale as a leader herself in those 11 years? What advice does Leyla give to young people considering whether to found a startup, join a startup or join a hyper-growth company?
  • Where do things start to break in the scaling of SaaS companies? What needs to be put in place to prepare for hyper-scale? What are the commonalities of where many founders go wrong in the scaling process?  
  • What does Leyla mean when she says, “growing up in product, you have to lead through influence”? How does Leyla think this influence can be created and maintained? How does Leyla think about the balance between effective influence and excessive influence?  
  • Why does Leyla believe that, “you can teach skills but you cannot teach empathy”? What have been her learnings from scaling teams when it comes to hiring and detecting candidates with true empathy? What can one do to nurture that empathy in the culture of the company?

60 Second SaaStr:

  1. What does Leyla know now that she wishes she had known at the beginning?
  2. What is the hardest element of Leyla’s role at Salesforce today?
  3. What does Leyla believe in SaaS that most around her disbelieve?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Leyla Seka

Mar 25, 2019
SaaStr 219: Atlassian President Jay Simons on How to Scale an Open Culture
21:17

At Atlassian, openness is core to everything the company does: employees can access most information on Confluence; "open company, no bullshit" is one of the company’s five values. But it can be risky. Atlassians knew the company was going public four months before it filed. The entire company was told about Atlassian selling its chat products Stride and Hipchat to its largest competitor in the space, Slack, four days before the news went out. Some would say that that level of openness is unnecessary, but Atlassian believes that trust and honesty are essential to maintaining the culture its worked so hard to build.

 

Missed the session? Here’s what Jay talks about:

  • What is driving growth in the cloud?
  • Does collaboration help founders drive growth forward?
  • How do you scale an open culture?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Mar 21, 2019
SaaStr 218: Twilio Founder, Jeff Lawson & SendGrid CEO, Sameer Dholakia on Why Developer First Is A Maturation In The Supply Chain Of Software & Why With Software Innovation Costs Being Lower Than Ever, Operators Must Maximise The Number of "At Bat" Oppor
38:28

Jeff Lawson is the Founder & CEO @ Twilio, the company building the future of communications allowing you to engage customers like never before on voice, SMS, WhatsApp or Video. Prior to their IPO in 2016, Twilio had raised over $250m in VC funding from some of the best in venture including USV, Bessemer, Salesforce and Techstars just to name a few. As for Jeff, prior to founding Twilio, Jeff was the Founder & CTO @ Nine Star Inc and enjoyed a spell at Amazon as a Technical Product Manager.

 

Sameer Dholakia is the CEO @ SendGrid, the category leader in email delivery, reaching half of the world’s digital users every 3 months. Last year Twilio acquired SendGrid bringing email into one seamless customer engagement platform. As for Sameer, prior to joining SendGrid, he spent 4 years at Citrix, where he drove the company’s product strategy for cloud infrastructure and server virtualization. Sameer joined the company in 2010, when Citrix acquired VMLogix, where he served as CEO and doubled revenues during each year of his tenure. Before that, he worked for 12 years at Trilogy, where he held key leadership roles helping the company grow from a start-up to a $300 million business.

In Today’s Episode We Discuss:

  • How Jeff came to found Twilio and what was that a-ha moment for him? How did Sameer enter the world of SaaS and come to be CEO @ SendGrid?
  • How did Jeff and Sameer assess the culture fit between the 2 companies when deciding whether or not to join forces? How did they formulate and approach creating a new set of values with the 2 companies coming together? How do they distinguish between culture and values? How can leaders both be authoritative and vulnerable simultaneously?
  • What does Jeff mean when he says, “the developer first approach is a maturation of the supply chain of software”? How has Jeff seen his original thesis for “developer first” evolve and change with time? What does truly special customer experience look like in the developer first model?  
  • In terms of product strategy, how do Jeff and Sameer approach when is the right time to release a second product? What does Jeff mean when he says, “you have to maximise the number of at bat opportunities you have”? Why does Sameer think that SendGrid waited too long to release additional product lines? What were his core learnings from that?
  • How do Jeff and Sameer think about what what truly special leadership looks like today? How do they approach speaking so that people will remember? What are some of their biggest tips to aspiring entrepreneurs with regards to that and team empowerment? Why do both Jeff and Sameer believe that so much of the management wisdom today is outdated?

60 Second SaaStr:

  1. What do Jeff and Sameer know now that they wish they had known at the beginning?
  2. The book they have gifted most often and why?
  3. What does it take to truly be a great board member?
  4. What do the next 5 years look like for Twilio? How big could it get?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Jeff Lawson

Sameer Dholakia

Mar 18, 2019
SaaStr 217: Stripe COO Claire Hughes Johnson on The Trapdoor Decisions to Avoid When Scaling
25:04

Formerly a senior leader at Google, Claire Hughes Johnson is now Chief Operating Officer at Stripe, where she’s helped guide the online payments firm through rapid growth. Stripe today has more than 1,400 employees and processes billions of dollars for millions of users worldwide. Scaling the company’s employee base, sales teams, marketing, and operations—all while preserving its culture—has required a laser focus on first principles, smart processes, and effective hiring.

Missed the session? Here’s what Claire talks about:

  • How to avoid trapdoor decisions when scaling
  • Lessons for scaling high-growth organizations

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Mar 14, 2019
SaaStr 216: Why Your Sales Team Is Not Working Together The Way You Think It Is, What Is Account Based Collaboration, How Can You Integrate It Into Your Organisation To Drive Conversion And Account Management & How To Prevent Silos Forming Within Your Tea
28:59

Dan Reich is the Founder & CEO @ Troops.ai, the startup that is the ultimate slackbot for sales teams. To date, Dan has raised over $17m in VC funding with Troops from many friends of the show including Felicis Ventures, Founder Collective, First Round, Nextview, Susa Ventures and even Slack. As for Dan, he is also the Co-Founder and President of TULA, a private equity backed health and beauty business that has developed the world's first line of probiotic skincare products. Before that, Dan was a Co-Founder of Spinback (acquired by Buddy Media in May 2011, then acquired by Salesforce in June 2012).

In Today’s Episode We Discuss:

  • How Dan made his way into the world of SaaS with the founding of Spinback? How that led to his founding of the ultimate slackbot for sales teams in Troops?
  • What does Dan really mean when he says “account based collaboration”? What is this a transition from? In terms of tracking and analysis, how does this change when making the move from tracking individual performance to team performance around an account? What can one do to actively implement this? What is key to a successful transition to this style of selling?
  • What does Dan mean when he says, “sales teams are not working together the way we think they are”? What can sales leaders do to actively ensure their sales team is acting in unison? Where do many sales leaders go wrong here? How does Dan think about post mortems when an account is lost or won? How does Dan prevent dips in morale when sharing the loss of a sale?
  • With scaling orgs, siloes are often created, why does Dan think many silos come into existence? At what stage does Dan really see them become a problem and cracks in the org begin to show? What can leaders do to instantly reduce the effect of silos? How does Dan think about controlling the noise to action ratio with the firehose of data at our disposal today?

Dan’s 60 Second SaaStr:

  1. What does Dan know now that he wishes he had known at the beginning?
  2. What is the right time to train your sales team?
  3. The right way to structure sales comp plans?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Dan Reich

Mar 11, 2019
SaaStr 215: Qualtrics Co-Founder and CEO Ryan Smith on The Things Nobody Tells You About an $8 Billion Acquisition
20:34

Qualtrics Co-Founder and CEO Ryan Smith sits down with SaaStr Founder and CEO Jason Lemkin as Ryan reflects on the survey software maker's acquisition by SAP this year. The company was acquired this November in an $8B deal ahead of its planned IPO. This is SaaStr’s founder favorites series where you can hear some of the best of the best of SaaStr Annual’s Speakers.

Missed the session? Here’s what Jason and Ryan talk about:

  • Why did Qualtrics turn down a $500M acquisition offer in 2012?
  • What did Qualtrics’ path to fundraising look like?
  • How to build lifelong customers
  • Capital efficiency (and dilution)

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Mar 07, 2019
SaaStr 214: New Relic CRO Erica Schultz on What It Takes To Successfully Scale Into Enterprise & How The Very Best Reps Build Relationships With Their Leads
32:41

Erica Schultz is Chief Revenue Officer @ New Relic, the company that gives you the real time insights your software driven business needs to innovate faster. Prior to their IPO, New Relic raised over $214m in funding from some of the best in the business including Benchmark, Insight Venture Partners and Blackrock, to name a few. As for Erica, under her CRO role, she leads all go-to-market functions including Marketing, Sales, Operations, Customer Success, Services, and Support. Prior to New Relic, Erica served as Executive Vice President of Global Sales and Customer Success at LivePerson and before that, Erica had a 16-year tenure with Oracle Corporation, where she founded and led numerous teams within the sales organization, including pioneering the company’s cloud business, and leading teams for North American and Latin American markets.

In Today’s Episode We Discuss:

  • How Erica made her way into the world of SaaS and came to be Chief Revenue Officer @ New Relic? What were some of her biggest takeaways from her incredible 16 year journey with Oracle?
  • Why does Erica believe that enterprise is a “company sport”? Why does each department need to re-platform when making the move to enterprise? How can founders know when is the right time to make the move from SMB to enterprise? Where does Erica often see founders make mistakes with this scaling?
  • How does the move to enterprise fundamentally impact the sales team? How does the structure of the sales team change with the move? How does the role of marketing change with the move to enterprise? How does this move impact the relationship between sales and marketing? How should compensation plans be altered with the move?
  • With the scaling of departments and teams, what has Erica seen work really well when it comes to making cross-functional teams communicate really well? What are the inflection points where Erica often see communication or process begin to breakdown? How does Erica ensure the team are still in the trenches with the clients despite the scaling?
  • From Erica’s experience, how do the very best sales reps build relationships with their prospects? Where do many go wrong? How much time does Erica believe reps should be given when it comes to translating relationships to dollars? What is the right way to think about payback period today?   

Erica’s 60 Second SaaStr:

  1. What does Erica know now that he wishes he had known at the beginning?
  2. The optimal relationship between CRO and CEO?
  3. The hardest element of being CRO @ New Relic?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Mar 05, 2019
SaaStr 213: Redpoint's Tom Tunguz on What Makes The Most Effective Free Trial, What Makes Good vs Great When It Comes To Benchmarks for Assisted vs Unassisted Conversion & Why Scoring Leads May Actually Be Dangerous
35:40

Tom Tunguz is General Partner @ Redpoint Ventures, the venture fund with a portfolio including the likes of Stripe, Netflix, Zuora, Hashicorp and Juniper Networks just to name a few. As for Tom, he joined Redpoint in 2008 and has since led investments in Kustomer, Looker, Expensify and Gremlin all prior guests on the show I hasten to add. He is also the co-author of Winning with Data: exploring the cultural changes big data brings to business. Tom has also been named on the Forbes Midas Brink list. Before joining Redpoint, Tomasz was the product manager for Google’s AdSense social-media products and AdSense internationalization.

In Today’s Episode We Discuss:

  • How Tom made his way from creating software with his father in Brazil to being GP and forefront figure in the SaaS investment community as a GP at Redpoint today?
  • Annual contracts: To what extent do annual contracts dominate today? How does this differ when comparing enterprise to SMB? Why does Tom think in the early days one should be wary of signing too many multi-year contracts? What are the dangers there? How does Tom think about calculating churn when it comes to multi-year contracts?
  • What were the findings on what good looks like when it comes to logo retention? How does this differ when comparing SMB to enterprise? What were the commonalities of leading indicators of churn? Is it fair to always surmise that when serving SMB one will always have a higher rate of churn? What is the right way to conduct a churn analysis?
  • Assisted vs unassisted: What does Tom believe are the leading benchmarks for both? How does this differ when comparing SMB to enterprise? How does the impact of a salesperson change the conversion rate? What time frame from SAL to closed lead suggests product market fit? What one question must all founders be asking in the sales process?
  • How does Tom think about constructing comp plans the right way today? How should comp plans differ when comparing AEs to customer success? Where should the responsibility for upsell lie, customer success or sales? Should sales commission be paid on renewals?  

Tom’s 60 Second SaaStr:

  1. What does Tom know now that he wishes he had known at the beginning?
  2. What is Tom’s favourite book and why?
  3. What is Tom’s most recent investment and why did he say yes?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Tom Tunguz

Feb 26, 2019
SaaStr 212: Who Must Fundamentally Own Renewals Within Your Organisation, Why Burying Customer Success Under Sales Does Not Work & The Biggest Truisms On Talent That Are False and So Dangerous with Nick Mehta, CEO @ Gainsight
38:33

Nick Mehta is the CEO @ Gainsight, the #1 customer success platform for corporate services, turning your customers into your best growth engine. To date Gainsight have raised over $156m from some of the world’s best VCs in the form of Lightspeed, Bessemer, Insight Venture Partners, Battery Ventures and Salesforce Ventures. As for Nick, prior to Gainsight he was the CEO @ LiveOffice where he grew cloud archiving ARR from $2m in 2008 to $25m in 2011 and drove and negotiated the acquisition by Symantec for $115m in cash. Before LiveOffice Nick was Senior Director of Product Management @ Symantec where he led $378 MM market-leading email archiving / security businesses managing over 180 people across 3 continents. I do also have to say a huge thank you to both Byron Deeter and Jason Lemkin for the intro to Nick over two years ago.

In Today’s Episode We Discuss:

  • How Nick made his way into the world of SaaS and came to lead the charge in the category creation of customer success as CEO with Gainsight? What were some of his big lessons from being CEO at 2 companies during 2 macro market crashes?
  • What does Nick mean when he says, “customer success will fail if it is just a role and not a strategy?” What can the leader and CEO do to imbue this company wide approach to customer success? What tangible actions are on offer? What works? Where do many make mistakes?
  • Nick has previously said, “burying customer success undel sales does not work”. Why does this have such a high rate of failure? What should the optimal sales to customer success relationship look like? What does Nick mean when he says, “product is to customer success what marketing is to sales”. How should product and customer success work together?
  • Why does Nick believe the mythology of the “A player” when business building is fundamentally dangerous? What can leaders and CEOs proactively do to ensure a diverse and differentiated talent pipeline? What question does Nick find most revealing in terms of one’s character and potential? Where do many go wrong in building and scaling their teams in SaaS?
  • Why does Nick push back against the “hire fast and fire fast” thesis? What are the negative consequences of it? Why is it short-sighted and premature in many cases? What does Nick suggest for individuals struggling to find their optimal role within an organisation? How much time does one give someone struggling to find their role?

Nick’s 60 Second SaaStr:

  1. Who must fundamentally own the renewal, sales or customer success?
  2. What Nick know now that he wishes he had known at the beginning?
  3. What would Nick most like to change in the world of SaaS?
  4. Most surprising action that has moved the needle for a company in terms of retention?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Nick Mehta

Feb 19, 2019
SaaStr 211: The Ultimate Guide To SaaS Pricing From Investors @ Benchmark, Matrix, Upfront Ventures & Operators @ Figma, Snyk and Kustomer
26:20

In Today’s Episode We Discuss:

  • David Skok: General Partner @ Matrix Partners: Why does David believe that all good products have at least one variable pricing axis? How can founders determine which variable they should choose for their product? What are the pros and cons?
  • Chetan Puttagunta: General Partner @ Benchmark: Why does Chetan believe we have seen a strong decline in the per seat pricing model? What are the major drawbacks of it? What are we seeing replace it? What has Chetan seen work well amongst his portfolio?     
  • Mark Suster: General Partner @ Upfront Ventures: What were Mark’s two biggest lessons on pricing from seeing the hyper-growth of Salesforce first hand? WHat does Mark advise founders when it comes to price anchoring and discounting? How does Mark view the sale of professional services with this in mind?
  • Amanda Kleha: Chief Customer Officer @ Figma: What were Amanda’s biggest learnings from running the Zendesk pricing playbook? What does Amanda mean when she says that successful pricing is broke up into 3 separate product features?   
  • Brad Birnbaum: Founder & CEO @ Kustomer:Why does Brad push back on the common suggestion of a “no man’s land in SaaS pricing”? Why is innovation in pricing actually detrimental to sales in most cases?
  • Guy Podjarney, Founder & CEO @ Snyk: How does Guy think about having a large enough base to test pricing strategies? How does Guy think about the balance between freemium and paid? Does one have to come first?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Feb 11, 2019
SaaStr 210: Why The Best Sales Reps Are Not Outgoing and Extroverted, Why Sales Reps Are Fundamentally Not Coin Operated and The Right Way To Structure Both Comp Plans and Sales Training with Bridget Gleason, VP of Sales @ Logz.io
32:02

Bridget Gleason is VP of Sales @ Logz.io, the startup that uses predictive analytics and machine learning to provide monitoring, troubleshooting and security. To date, Logz have raised over $45m in funding from the likes of Openview, 83North and Vintage just to name a few. As for Bridget, she has the most incredible track record. Before Logz, Bridget was VP of Corporate Sales @ Sumo Logic where she drove ARR up by a record 237%. Prior to SumoLogic, Bridget was VP of Sales @ YesWare where she increased MRR per rep by 450%. Finally before YesWare, she was VP of Sales @ Engine Yard, where she tripled monthly recurring revenue, over course of 3+ year tenure, in 3 key leadership roles.

In Today’s Episode We Discuss:

  • How Bridget made her way into the world of sales and became the sales leader she is today, having started in the world of marketing?
  • Having led and scaled numerous sales teams, does Bridget agree the best sales reps are outgoing and extroverted? How does the successful profile of a sales rep depend on (1) whether you are selling to SMB or enterprise? (2) The stage of the company? How can one stress test the character type of the candidate pre-hire in the interview stage?     
  • Does Bridget believe that sales reps really are as coin operated as many suggest? Why is that potentially an unfair position to take? How does Bridget think about structuring the right comp plans for her team? What other methods of incentivisation does Bridget believe works equally as efficiently?    
  • Does Bridget believe that you should pay sales rep commissions on services revenue? Should one pay the same or lower commissions on renewals? Should multi-year deals be paid upfront? How does one structure commissions for the sales team with that in mind?  
  • When does Bridget believe is the right time to hire (1) your first sales reps? (2) Your first VP of Sales? Why does Bridget believe that 70% of VP of Sales positions do not work out in the first 9 months? What can founders do to increase the likelihood of success within their VP of Sales role? Where do many go wrong?  

Bridget’s 60 Second SaaStr:

  1. What does Bridget know now that she wishes she had known when she started in SaaS?
  2. SDR’s are the most important function in the sales process, agree or not and why?
  3. Sales training, what works? What does not?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Bridget Gleason

Feb 04, 2019
SaaStr 209: The 3 Components To Successful SaaS Pricing, Lessons From Seeing Zendesk Scale From 12 to 2,000 and How To Ensure Successful Cross-Functional Communication with Amanda Kleha, Chief Customer Officer @ Figma
37:30

Amanda Kleha is the Chief Customer Officer @ Figma, the startup that allows you to turn ideas into products faster through design, prototyping and feedback gathering, all in one place. To date, Figma have raised over $42m in VC funding from some of the best in the business including Index Ventures, Kleiner Perkins, Greylock Partners and former guests on 20VC, Daniel Gross and Adam Nash. As for Amanda, prior to Figma, she held numerous roles at Zendesk including SVP of Marketing and Sales Strategy. Amanda joined Zendesk as the first marketing hire and over the next 7 years Zendesk grew to over 2,000 employees. Before Zendesk, Amanda worked on the marketing team for Google’s Enterprise SaaS businesses. If that was not enough Amanda is also an advisor at Airtable and Smartling.

In Today’s Episode We Discuss:

  • How Amanda made her way into the world of SaaS and came to join Zendesk as their first marketing hire seeing the company scale to over 2,000 over the next 7 years?
  • What were some of Amanda’s biggest learnings from seeing Zendesk scale from 12 to 2,000? How does one determine those that can vs cannot grow with the business? What is the sign a stretch VP is a stretch too far? How does Amanda balance between a culture of risk taking but also not accepting failure to easily?     
  • How does Amanda like to run the interview process? Why does Amanda like to not show emotion when interviewing a candidate? What are the benefits of this for the brand of your company? What single question does Amanda find most revealing in showing the abilities and character of a candidate in an interview?   
  • What does Amanda mean when she says “pricing is made up of 3 components”? Where does Amanda believe most people go wrong with pricing? Is there such thing as no man’s land in SaaS pricing? How does Amanda think the go-to-market has to change with every stage of development? What are the challenges with this?
  • How does the structure of decision-making change with scale? What are the inflection points? When does both decision-making and communication tend to break down? What can be done to ensure seamless cross-functional communication across the org? Where do most people fail here?   

Amanda’s 60 Second SaaStr:

  1. What does Amanda know now that she wishes she had known when she started in SaaS?
  2. Is there such thing as no man’s land in SaaS pricing?
  3. How to ensure customer support is strategic and not just reactionary?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Amanda Kleha

Jan 28, 2019
SaaStr 208: SendGrid Board Member, Anne Raimondi on Why We Have To See Innovation In SaaS Pricing, Why Everyone in SaaS Orgs Has To Be Product People & Why Humans Can't Scale More Than 100% YoY & What That Means For Scaling Orgs
36:00

Anne Raimondi has more than 20 years experience driving growth at startups and building them into nationally recognized brands. She has served as a leader and executive for technology innovators including Zendesk, Survey Monkey, Blue Nile, and eBay. Anne is also a Lecturer in Management at Stanford Graduate School of Business, teaching two popular courses, “Startup Garage” and “POWer: Building the Entrepreneurial Mindset.” She currently serves on the board of directors for SendGrid (NYSE: SEND) and MyHealthTeams. If that was not enough, Anne is also an active angel investor with an incredible portfolio including the likes of Canva, ipsy, and Minted just to name a few.

In Today’s Episode We Discuss:

  • How Anne made her way into the world of startups with Zendesk? How did seeing the hyperscaling of Zendesk impact Anne’s operational approach and mindset?
  • Does Anne agree that certain individuals are destined for certain stages of company development? What are the leading indicators that one can or cannot scale? What are the inflection points in company growth where process tend to break? What can managers do to provide security in these times of change?   
  • Why does Anne believe that everyone should be a product person in SaaS? What are the inherent benefits of this product centricity? How does the element of product centricity change when catering to 2 customers, CIO and consumer? How does Anne advise on this issue of agency?  
  • How does Anne approach optimising internal decision-making processes? Where do many leadership teams make mistakes here? What is the right way for leadership teams to communicate their decisions to the wider team? How does Anne approach ensuring cross-functional communication at scale?
  • How has Anne seen her style of board membership change over the last 8 years? What has been an inflection point that has changed the way she thinks about what it takes to be a great board member? Who has been the best board member Anne has worked with? What made them so special?  

Anne’s 60 Second SaaStr:

  1. What does Anne know now that she wishes she had known at the beginning?
  2. The right way for founders to view competition?
  3. What would Anne most like to change in the world of SaaS today?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Anne Raimondi

Jan 21, 2019
SaaStr 207: 13 Years To 20 People; 3 Years Later 350 People and $50m ARR, Why Thinking There Is A Price Point You Need For A Rep Is BS & Why SMB First Works And You Must Not Design For Enterprise
30:57

Jason VandeBoom is the Founder and CEO of ActiveCampaign, a sales and marketing automation platform that enables small businesses around the world to meaningfully connect and engage with their customers. Jason founded the company in 2003 and under Jason's leadership, ActiveCampaign has flourished from a successful but small company and then in 2013, they transition to SaaS, since they have grown to more than $50 million in ARR in less than five years, while still maintaining profitability and its culture. They have also only raised a single $20m PE round to accelerate their growth, making them a market leader in terms of funds raised/ARR generated.  

In Today’s Episode We Discuss:

  • How Jason made his way into the world of SaaS and came to found ActiveCampaign?
  • Why is Jason so bullish that “SMB first, works”? What are the inherent benefits from starting at SMB? How does it affect product feedback? How does it affect how you build and scale your team? How does one start to layer in market and enterprise over time? Why does it give you additional leverage?  
  • What does Jason think is the right way to scale your sales team> Why does one not need funding to scale sales teams? When does Jason believe is the right time to hire your first VP of Sales? What were the biggest mistakes that Jason made in the scaling of his sales team? Why should hire 3 reps to start at one time?  
  • How does Jason view the current fundraising environment? Why does Jason believe that “no one cares if you get funding”? Why does Jason believe there is a fear around needing fast growth? Who is to blame for this? How should founders in the messy middle feel when seeing large fundraises in the media?
  • Why does Jason believe that all leaders need to be consuming all feedback? How does Jason consume feedback on a daily basis? What metrics and elements does he look for in this assessment? How has Jason’s role changed over the 16-year CEOship? Does it get easier over time in Jason’s mind? What has been the biggest challenge?

Jason’s 60 Second SaaStr:

  1. What does Jason know now that he wishes he had known at the beginning?
  2. No man’s land of SaaS pricing, exist or a myth?
  3. Multi-year deals, all they are cracked up to be or overrated?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: 

Jason Lemkin

Harry Stebbings

SaaStr

Jason VandeBoom

Jan 15, 2019
SaaStr 206: 4 Core Considerations Startup Founders Must Recognise When Pricing Their Product, Why Being Good At Sales Won't Make You A Great Sales Leader and Why Boring Is Better Than Sexy When It Comes To Winning Your Market with Ryan Barretto, SVP of Gl
27:45

Ryan Barretto is the SVP of Global Sales at Sprout Social, a leading provider of social media engagement, advocacy and analytics solutions for business. To date they have raised over $111m in funding from the likes of NEA, Goldman Sachs and their very recently announced $40m Series D led by Future Fund.  At Sprout Social Ryan oversees both the Sales and Customer Success organizations. Prior to Sprout, he was the VP of Global Sales at Pardot–a Salesforce company. At Pardot, Ryan's team tripled revenue growth in two years, making Pardot one of Salesforce's fastest growing businesses and during his 10 year tenure at Salesforce he saw the company grow from $180m to $7.5Bn.

In Today’s Episode We Discuss:

  • How Ryan made his way into the world of SaaS with Salesforce over 13 years ago? What were some of Ryan’s biggest takeaways from seeing Salesforce scale from $180m to $7.5Bn?
  • Why does Ryan think that it is lazy to believe that you have to pick a market and you can’t have them all? How can one approach the element of very different messaging being required for SMB vs enterprise? How can one do both? How does that change the structure of the team? How can one build a product with the simplicity of SMB and functionality of enterprise?  
  • When it comes to winning the market, what does Ryan mean when he says, “boring is better than sexy”? What are the 4 elements all founders must consider when pricing their SaaS product? Where does Ryan see many go wrong with pricing? When serving SMB, how can one provide enterprise quality customer support? How does Ryan feel about customisation? What number justifies it?  
  • Why does Ryan believe that being good at sales won’t make you a great sales leader? What is needed to make the transition? What can sales reps do to learn and bridge that gap? What has worked for Ryan in the past? Where has Ryan seen many go wrong here? What 3 elements does Ryan look for in al additions to the team?
  • What is the number 1 issue that is preventing people building truly diverse teams? How can we change our job descriptions to make the more inclusive? How can we expand our candidate pool to include more diverse people than usual? What can leaders do to build environments of inclusion where people can really bring their full selves to work?

Ryan’s 60 Second SaaStr:

  1. What does Ryan know now that he wishes he had known at the beginning?
  2. Sales rep productivity, what is good to Ryan?
  3. What motto or quote does Ryan frequently revert back to? Why?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Ryan Barretto

Jan 07, 2019
SaaStr 205: The Secret To Building A Truly Successful Freemium Product | The 3 Classes of Product & How To Think About Feature Prioritisation | A Framework For Building Strong Cross-Functional Communication Across Locations with Guy Podjarny, Founder & CE
37:53

Guy Podjarny is the Founder & CEO @ Snyk, the developer-first solution that automates finding and fixing vulnerabilities in your dependencies. To date, Guy has raised over $32m in VC funding from Snyk from some of the great of venture including Accel, GV, our friends at Boldstart and Canaan Partners, just to name a few. As for Guy, prior to Snyk, he was the CTO of Akamai’s Web Performance Business following their acquisition of his startup, Blaze.io. Before founding Blaze, Guy built Web Application Security products, including the first Web App Firewall (AppShield), Dynamic Application Security Testing tool (AppScan) and Static Application Security Testing tool (AppScan Dev Edition). Fun fact on Guy, he is the holder of 18 patents related to security and performance.

In Today’s Episode We Discuss:

  • How Guy made his way into the world of SaaS and came to found one of the hottest open source companies of our day in the form of Snyk?
  • How does Guy navigate between the difficult balance of going wide on market and shallow on product or narrow in market and deep in product? What is the decision-making process? What does Guy advise founders on feature prioritisation in the early days? Does Guy agree if you are not embarrassed by V1, you have shipped too late? How does support provide a feedback loop on what to build next?  
  • Why does Guy believe that, “successful freemium requires giving away your secret sauce”? How can one give away enough secret sauce in freemium without giving away too much people don’t buy? How does freemium fundamentally alter your relationship to revenue? Where does Guy see many going wrong when pursuing the freemium model?  
  • How does Guy think about the problem of agency with developers using the product but having to sell to CIOs? What 2 things can be done to make this sell easier? What does Guy believe is the right framework to think about pricing through? Why is transparency in enterprise pricing not always optimal?
  • What does Guy believe is required to have strong and seamless communication across functions and locations? How has Guy seen this change over time and with increased locations? Where does Guy see many going wrong when trying to scale team across location?   

Guy’s 60 Second SaaStr:

  1. How does Guy know when is the right time to hire your first sales person?
  2. How did Guy learn to let go and trust his team?
  3. What does Guy know now that he wishes he had known at the beginning?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: 

Jason Lemkin

Harry Stebbings 

SaaStr

Guy Podjarny

Dec 17, 2018
SaaStr 204: 2018's Most Downloaded Episode, Claire Hughes Johnson, COO @ Stripe
33:04

Claire Hughes Johnson, COO @ Stripe the new standard in online payments that handles billions of dollars of business every year for forward thinking businesses around the world. To date, Stripe has raised over $680m in funding from some of the very best in the business including Sequoia, Founders Fund, General Catalyst, Thrive, CapitalG, Kleiner Perkins and Tiger Global. As for Claire, prior to Stripe she spent over 10 years at Google in a range of different roles from VP of Google's self-driving car division to VP of Global Online Sales to VP of Google Offers. At Stripe, Claire has helped take Stripe global in February 2016 with the launch of Atlas, a toolkit that enables any business, anywhere in the world, to incorporate in the United States. If that was not enough, Claire is also a Board Member @ Hallmark Cards.

In Today’s Episode We Discuss:

  • How Claire made her way into the world of SaaS with Stripe following her leading of Google’s self-driving car division?
  • What does Claire mean when she discusses “founding documents”? What is the right way to go about creating them? What element do they need to contain? How can one optimise internal decision-making process with these documents? What question must one always try and ask when making big decisions?
  • How does Claire define a truly special COO? What does that truly great look like? When is the right time for founders to hire that COO? Where do the majority of people go wrong in their assessment of when and what they need in a COO? What is the optimal relationship one can have between CEO and COO?
  • How does Claire think about what Stripe have done right to hire so effectively at scale? What does it take in terms of benchmarks and standards to do so? What does Claire mean when she says you have to step function up your capabilities with scale? What are the core challenges in hiring at scale?  

Claire’s 60 Second SaaStr:

  1. What would Claire say are her biggest strengths and weaknesses?
  2. What does Claire know now that she wishes she had known at the beginning?
  3. A moment in Claire’s life that has served as an inflection point and changed the way she thinks?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

 

Jason Lemkin

Harry Stebbings

SaaStr 

Claire Hughes Johnson

Dec 10, 2018
SaaStr 203: Why Every Startup Should Bootstrap At Some Stage, Why Transparency In Pricing Is Not Always Optimal & Why We Have To Embrace That Service Is An Essential Part of SaaS Today with Krish Subramanian, Founder & CEO @ Chargebee
29:11

Krish Subramanian is the Founder & CEO @ Chargebee, the startup that lets you go beyond billing, payments and recurring invoices — to delivering subscription experiences that "wow". To date, Chargebee have “wowed” some of the world’s leading VCs to the tune of $24m including the likes of Insight Venture Partners, Tiger Global and Accel Partners. As for Krish, under Krish’s leadership the team has grown to over 200 people and over 5,000 clients making it one of the next generation in truly global SaaS businesses started in India.

In Today’s Episode We Discuss:

  • How Krish made his way into the world of SaaS and came to found one of India fastest growing SaaS companies in Chargebee?
  • Why does Krish believe that every SaaS company should bootstrap at some stage? What are the inherent benefits to these capital constraints? What are the drawbacks to not having the capital reserves? What was the inflection point for Krish in realising he wanted to go big and raise from Insight?  
  • Why does Krish believe that it is wrong to think of the word “service” as being negative in SaaS? What are some of the foundational benefits to building out a strong services division? How does Krish think about what makes for good margins in services businesses? How can one prevent themselves from being reliant on service revenue?
  • Why does Krish believe that transparency is not always good when it comes to SaaS pricing? What are the cons of transparent pricing? Why does Krish believe if you are going to try freemium, it has to be from the beginning? How does Krish think about reinventing the wheel vs copying when it comes to pricing? How does Krish think about installing usage based pricing without disincentivizing usage? How can one do it?

Krish’s 60 Second SaaStr:

  1. What does Krish know now that he wishes he had known at the beginning?
  2. What moment in Krish’s life has served as an inflection point and changed the way he thinks?
  3. What does Krish believe that most around him disbelieve?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: 

Jason Lemkin

Harry Stebbings

SaaStr

Krish Subramanian

 

Dec 03, 2018
SaaStr 202: Intercom COO Karen Peacock on Lessons Learned Running A $2.2Bn Line of Business at Intuit, The Most Important Metric You Probably Aren't Tracking & Why, When and How To Hire Your COO
36:57

Karen Peacock is the COO @ Intercom, the company that provides a new and better way to acquire, engage and retain customers. To date, Intercom have raised over $240m in VC funding from some of the very best in VC including GV, Kleiner Perkins, Bessemer, ICONIQ and then individuals such as Mark Zuckerberg, John Collison, Biz Stone and Andy McLoughlin. As for Karen, prior to Intercom, she spent an incredible 17 years at Intuit leading all of Intuit’s small business products and services worldwide, a $2.2B business including QuickBooks, Accounting, Payments, and Payroll. As part of that, Karen managed a team of 500 and helped build one of the world’s largest SaaS businesses.

In Today’s Episode We Discuss:

  • How Karen made her way into the world of SaaS with Intuit and how that led to becoming COO @ Intercom today? What were Karen’s biggest takeaways from her time at Intuit?
  • What does Karen mean when she says “watch what customers do, not what they say”? How does Karen think about the difference between being customer driven vs customer informed? Why is it important to fall in love with the problem and not the solution as an entrepreneur?
  • Karen has grown Intercom from 350 to 600 in 18 months, what would Karen’s biggest advice and learnings be when it comes to team assembly and hiring the best? What can one do to stress test the fit of the candidate pre-hire? What does Karen always find to be the most revealing questions to ask?
  • When does Karen believe is the right time to hire a COO? How does one know when they have the right COO fit? What are some best practices for onboarding a new COO? What is the optimal relationship between CEO and COO?
  • Karen has seen incredible scaling first hand both with Intercom and Intuit, what would some of her biggest takeaways and advice be on scaling? Where does Karen see many make mistakes in the scaling phases? What does Karen mean when she speaks about “the most important metric that you probably aren’t tracking?”

Karen’s 60 Second SaaStr:

  1. What does Karen know now that she wishes she had known at the beginning?
  2. What motto or quote does Karen frequently revert back to?
  3. What is the most challenging element in Karen’s role today?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: 

Jason Lemkin

Harry Stebbings

SaaStr

Karen Peacock

Nov 26, 2018
SaaStr 201: How To Prioritise Your Sales Pipeline, Why You Should Spend Your Time on the 10% Least Likely Leads & Why The Secret To Success In Sales Is "Calls Between The Calls" with Hannah Willson, VP Sales @ Rainforest QA
28:03

Hannah Willson is the VP of Sales @ Rainforest QA, the on-demand QA solution that allows companies to discover problems that affect the customer experience before the code hits production. To date, Rainforest have raised over $40m in funding from some of the very best in SaaS including the legendary Byron Deeter @ Bessemer, Jason Lemkin @ SaaStr, Marc Benioff himself, Andreesen Horowitz and YC. As for Hannah, she has over 10 years of experience leading sales and customer teams at both startups and publicly traded companies including seeing the first hand hyper-growth of Zenefits in their heyday and being VP of BD, Sales and Customer Renewals for the western half of the US at HelloWallet, prior to their acquisition by Morningstar.

In Today’s Episode We Discuss:

  • How Hannah made her way into the world of SaaS and enterprise sales, came to join Zenefits in their heyday and how that led to her move to VP of Sales @ Rainforest?
  • How does Hannah think about time allocation and prioritisation of time across leads and the sales pipeline? WHat can AEs do in terms of optimising their win rate of opportunities? How important a role should discounting play in winning potential leads? Does Hannah optimise for quality or quantity of logos in the early days?
  • What does Hannah mean when she says the secret to success is “the calls between the calls”? How do these vary both in content and tone to traditional sales calls? Why must AEs be willing to open up and be vulnerable with leads? What can managers do to engender this? What is the optimal relationship for AEs and product team?
  • What does Hannah believe is the right mechanism for feedback delivery? What has worked well for her in the past? Where does Hannah see many today going wrong? What guidelines need to be put in place to ensure this candid and transparent feedback is effective?

Hannah’s 60 Second SaaStr:

  1. What does Hannah know now that she wishes she had known at the beginning?
  2. What does Hannah believe embodies good sales rep productivity?
  3. What is Hannah’s fave SaaS reading material?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Nov 19, 2018
SaaStr 200: Should SaaS Startups Start At SMB and Scale To Enterprise or Vice Versa, What It Takes To Make The Transition From CTO To CEO & The Right Way To Think About SaaS Pricing Today With Brad Birnbaum, Founder & CEO @ Kustomer
34:45

Brad Birnbaum is the Founder & CEO @ Kustomer, the first intelligent platform for customer experience that enables you to know everything about every customer. To date Brad has raised over $38m in funding for Kustomer from some of the very best in the SaaS business including Tomasz Tunguz @ Redpoint, Ed Sim @ Boldstart, Canaan Partners, Box Group and Social Leverage just to name a few. Previously he was the Co-founder of Assistly, which was acquired by Salesforce and became Desk.com. Prior to that, he was CTO for Talisma and Co‑founder & CTO of eShare Technologies. In addition, Brad was also the CTO @ Sean parker’s Airtime and VP of Engineering with Salesforce.

In Today’s Episode We Discuss:

  • How Brad made his way into the world of customer experience and SaaS over 20 years ago?
  • This is Brad’s 4th time at the roadshow, what does Brad believe are the core benefits of repeat entrepreneurship? How did his prior experience change his operating mentality with Kustomer? What has he done differently this time? What worked and he has kept the same?
  • Brad has made the transition from CTO to CEO, how did he find this transition? What were some of the most challenging elements? What have been some of the biggest surprises? What advice would Brad have for other CTOs who have made or are thinking about making the transition?
  • Brad initially served SMBs with Kustomer but now primarily focuses on mid-level, what would Brad’s biggest advice be when it comes to finding the right go-to-market strategy for you? How did their transition alter their approach to pricing, product, messaging and distribution? Where does Brad see many people go wrong on go-to-market?

Brad’s 60 Second SaaStr:

  1. What does Brad know now that he wishes he had known at the beginning?
  2. When is the right time to pour fuel on the company fire?
  3. What would Brad most like to change in the world of SaaS?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Brad Birnbaum

Nov 12, 2018
SaaStr 199: Betterment Founder, Jon Stein on The 3 Key Roles For A SaaS CEO, How To Retain Startup Culture As You Scale Past Startup Stage & The Most Telling Questions In Candidate Interviews To Stress Test Culture-Fit
27:26

Jon Stein is the Founder & CEO @ Betterment, the online financial advisor built for people who refuse to settle for average investing. To date, Jon has raised $275m in VC funding with Betterment from the likes of Bessemer Ventures Partners, Menlo Ventures, Kinnevik and Francisco Partners, just to name a few. Prior to founding Betterment, Jon spent 4 years as a consultant at First Manhattan Consulting Group where he really honed his experience in working with banks and brokers including revitalizing a bank in Australia with the launch of a best-in-market auto-finance offering, resulting in 50% lift to revenue. As a result of his phenomenal success with Betterment Jon has won many awards including Fortune’s 40 Under 40.

In Today’s Episode We Discuss:

  • How Jon made his way into the world of startups and came to found democratize the world of investing with Betterment?
  • When does Jon believe is that critical moment when the founding team must hire their first employee? What is the right strategy to build the candidate pipe for hiring those first employees? Where does Jon see many go wrong here? What 1-2 questions does Jon always find the most enlightening to ask in the interview?
  • Once hired, what have been some of Jon’s biggest lessons in terms of optimising the onboarding experience and the first 60 days? How has their process changed over time? How does Jon determine when a stretch candidate is a stretch too far? If so, what does Jon believe is the right way to let go of an individual?
  • What does Jon believe to be the 3 core roles of the CEO in any company today? From those, what has Jon found most challenging? What did he do to level up and overcome the challenges? How does Jon approach transparency with the team in delicate cases like fundraising and acquisition etc?
  • With the team and product in place, scale can occur, what are the 2-3 things that all companies need to focus on when product market fit has been achieved? How does Jon determine when is the right time to really put the pedal to the metal and scale?

Jon’s 60 Second SaaStr:

  1. Jon’s favourite book and why?
  2. What does on know now that he wishes he had known at the beginning?
  3. What is Jon’s biggest strength and weakness?

Read the full transcript on our blog. 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Jon Stein

Nov 05, 2018
SaaStr 198: Decision-Making in B2B Marketing; Instinct or Data-Driven, How To Create True Alignment Between Sales and Marketing & Why Sometimes You Have To Throw The Marketing Playbook Out The Window with Maria Pergolino, CMO @ Anaplan
33:42

Maria Pergolino is the CMO @ Anaplan, the company that allows you to accelerate decision-making with effective planning. To date, Anaplan have raised over $299m in funding from the likes of Meritech, Salesforce Ventures, Shasta, DFJ Growth and more incredible names. As for Maria, prior to Anaplan, Maria was Senior Vice President of Global Marketing and Sales Development at Apttus, where she directed go-to-market strategy, sales development, customer advocacy, demand generation, strategic events and communications initiatives. She also has held leadership positions at Marketo, Shunra Software (acquired by Hewlett-Packard), and Chubb Ltd. It’s also important to note, Maria is renowned for building world-class teams that drive growth, product differentiation, and category development.

In Today’s Episode We Discuss:

  • How Maria made her way into the world of B2B marketing? What were her biggest lessons from the days of Marketo?
  • How does Maria balance between instinct driven decision making vs data-driven in B2B marketing? Is there anything wrong with instinct driven? How can marketers confidently back up their thesis with substantive proof? How does one successfully sell that to leadership?
  • Maria is famous for rallying teams around her ideas, what has Maria found to be core to the success in gaining this collective approval and excitement? What is the right way to approach the marketing portfolio of strategies as a whole? What channel or segment is Maria currently most excited for?
  • How does maria evaluate the current event landscape in terms of effectiveness? Are we in a B2B event bubble? How can companies determine whether this is the right strategy for them? Would Maria agree with Joe Chernov, “to do events, you have to have an appetite for losing money? What does Maria and her team do to get the most out of events?
  • What does the term “marketing playbook” really mean to Maria? What does Maria mean when she suggests that marketers can let their own playbook get in the way? Why does maria think it is absurd for there to be misalignment from sales and marketing?

Maria’s 60 Second SaaStr:

  1. What does Maria know now that he wishes he had known at the beginning?
  2. Who does Maria believe is killing it in B2B marketing today?
  3. Advice commonly stated in SaaS that Maria disagrees with?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Maria Pergolino

 

 

Oct 29, 2018
SaaStr 197: Partnerships: When Is The Right Time, What is The Right Partnership, How To Determine Between An Individual That Can Scale with The Company vs One That Cannot & How To Make Fast Decisions When You Don't Have Data To Lean on with Cristina Cordo
33:31

Cristina Cordova leads the Payments Partnerships and Platform Partnerships teams at Stripe, the new standard in online payments that handles billions of dollars of business every year for forward thinking businesses around the world. To date, Stripe has raised over $680m in funding from some of the very best in the business including Sequoia, Founders Fund, General Catalyst, Thrive, CapitalG, Kleiner Perkins and Tiger Global. As for Cristina, at Stripe she manages partnerships with some of the biggest global players including Apple Pay, Google Pay, WeChat Pay and more and has also held roles such as Head of Diversity and Inclusion and Manager of Partner Engineering. Prior to Stripe, Cristina was Head of Business Development @ Pulse (acq by LinkedIn) and was in the marketing team at Tapulous (acq by Disney).

In Today’s Episode We Discuss:

  • How Cristina made her way into the world of SaaS and came to be Head of Partnerships at one of the fastest growing startups in the world, Stripe?
  • Does Cristina agree with the common notion that certain people are destined for certain stages of a company’s life? How can one determine whether some has the ability to scale or not? What are the leading indicators? What have been some of Cristina’s biggest lessons in scaling from 28 at Stripe to 1,300?
  • What does Cristina believe is the key to success when it comes to adapting to new roles? What worked? What did not work? Where does Cristina see many go wrong? How should employees think about title both when joining and when at a high growth company? What is the right way for them to think about and approach equity?
  • What does Cristina believe is so special about partnerships with early stage startups? How can partnerships be fundamentally dangerous for early stage companies? How can startups determine when is the right time to engage with partners? What are the key questions and terms startups should focus on when partnering with incumbents?
  • What makes Cristina lean in on a partnership for Stripe? What does Cristina believe is the right way to communicate this excitement and set expectations? For the larger player, what does the optimal agreement look like? What are the commonalities in the reasons that Cristina passes on potential partnerships?

Cristina’s 60 Second SaaStr:

  1. What does Cristina know now that she wishes she had known at the beginning?
  2. Who is killing it in SaaS partnerships today?
  3. When is the right time to hire a Head of Partnerships?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

 

Jason Lemkin

 

Harry Stebbings

 

SaaStr

 

Cristina Cordova

Oct 22, 2018
SaaStr 196: Stripe COO Claire Hughes Johnson on How The Best Leaders Inspire with Confidence and Stability, The Key To Successful Decision-Making & How To Hire Quality Teams At Scale
30:02

Claire Hughes Johnson is the COO @ Stripe, the new standard in online payments that handles billions of dollars of business every year for forward-thinking businesses around the world. To date, Stripe has raised over $680m in funding from some of the very best in the business including Sequoia, Founders Fund, General Catalyst, Thrive, CapitalG, Kleiner Perkins and Tiger Global. As for Claire, prior to Stripe she spent over 10 years at Google in a range of different roles from VP of Google's self-driving car division to VP of Global Online Sales to VP of Google Offers. At Stripe, Claire has helped take Stripe global in February 2016 with the launch of Atlas, a toolkit that enables any business, anywhere in the world, to incorporate in the United States. If that was not enough, Claire is also a Board Member @ Hallmark Cards.

In Today’s Episode We Discuss:

  • How Claire made her way into the world of SaaS with Stripe following her leading of Google’s self-driving car division?
  • What does Claire mean when she discusses “founding documents”? What is the right way to go about creating them? What element do they need to contain? How can one optimise internal decision-making process with these documents? What question must one always try and ask when making big decisions?
  • How does Claire define a truly special COO? What does that truly great look like? When is the right time for founders to hire that COO? Where do the majority of people go wrong in their assessment of when and what they need in a COO? What is the optimal relationship one can have between CEO and COO?
  • How does Claire think about what Stripe have done right to hire so effectively at scale? What does it take in terms of benchmarks and standards to do so? What does Claire mean when she says you have to step function up your capabilities with scale? What are the core challenges in hiring at scale?  

Claire’s 60 Second SaaStr:

  1. What would Claire say are her biggest strengths and weaknesses?
  2. What does Claire know now that she wishes she had known at the beginning?
  3. A moment in Claire’s life that has served as an inflection point and changed the way she thinks?

Read the full transcript on our blog.

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Jason Lemkin

 

Harry Stebbings

 

SaaStr

 

Claire Hughes Johnson

Oct 15, 2018
SaaStr 195: How To Truly Understand The Politics of Selling to Enterprise, Why Current Org Charts Are Upside Down and What Your Customer Success Team Has To Be Obsessed with Doing with Dan Reich, Founder & CEO @ Troops.ai
30:16

Dan Reich is the Founder & CEO @ Troops.ai, the startup that is the ultimate slackbot for sales teams. To date, Dan has raised over $17m in VC funding with Troops from many friends of the show including Felicis Ventures, Founder Collective, First Round, Nextview, Susa Ventures and even Slack. As for Dan, he is also the Co-Founder and President of TULA, a private equity backed health and beauty business that has developed the world's first line of probiotic skincare products. Before that, Dan was a Co-Founder of Spinback (acquired by Buddy Media in May 2011, then acquired by Salesforce in June 2012).

In Today’s Episode We Discuss:

  • How Dan made his way into the world of SaaS with the founding of Spinback? How that led to his founding of the ultimate slackbot for sales teams in Troops? How the experience with Spinback affected his operating mindset with Troops today?
  • Why does Dan believe that the current modelling of org charts is fundamentally upside down? How does Dan thi