Sales Players
By Jesse Woodbury
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Category: Entrepreneurship
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Episodes: 205
Description
The #1 resource for top players in Tech Startup Sales. Hosted by Jesse Woodbury, an expert in early-stage startup selling, Sales Players features weekly, actionable ideas for reps, founders, and operators by exploring the mindset, skills, and tools high performers use to generate pipeline, close deals, and build wealth in Tech Sales.
| Episode | Date |
|---|---|
|
Making the Most of Your Tech Sales Career
|
Oct 17, 2025 |
|
Lessons on Building a Personal Brand from 5 Years of Podcasting
|
Sep 19, 2025 |
|
20 Questions I Use to Stress-Test My Deals
|
Sep 17, 2025 |
|
What I’m Hearing: Sales Trends Shaping Tech in 2025
|
Sep 10, 2025 |
|
How I Re-Engage Closed-Lost Opportunities
|
Aug 28, 2025 |
|
5 Habits That Close More Deals
|
Aug 19, 2025 |
|
Your Network Is Doing More for Your Sales Career Than You Think
|
Aug 13, 2025 |
|
5 Ideas for Turning Your Sales Skills Into Extra Income
|
Aug 09, 2025 |
|
Why Reps Are Ditching Managers for AI Roleplay with Sriharsha (Sai) Guduguntla of Hyperbound
|
Jul 31, 2025 |
|
The Metrics That Matter Most in Tech Sales
|
Jul 19, 2025 |
|
What My Former Sales Leader Taught Me About Red Zone Selling with Vince Beese
|
Jun 26, 2025 |
|
20 Sales Plays I Run When Nothing Else Is Working
|
Jun 21, 2025 |
|
Building Financial Security as a Tech Seller
|
Jun 14, 2025 |
|
The Anonymous Tech Seller Who Built a 6-Figure Side Hustle with "Fidel Cache Flow"
|
Jun 11, 2025 |
|
23 Absolute Truths About Enterprise Selling
|
Jun 09, 2025 |
|
What Top Tech Sales Candidates Do Differently
|
Jun 06, 2025 |
|
Top Tech Sellers Share These 10 Traits
|
Jun 04, 2025 |
|
What I Learned (the Hard Way) as a Founding AE
|
May 28, 2025 |
|
This Is Exactly How I Approach Cold Calls Every Day
|
May 21, 2025 |
|
Want Bigger Deals? Learn the Product
|
May 15, 2025 |
|
A Week in My Life: Tech Sales, Family, Fitness & Side Projects
|
May 10, 2025 |
|
Why You're Still an SDR (and What to Do About It)
|
May 07, 2025 |
|
Why You Should Hold Off on Going Fully Remote in Your Career
|
May 01, 2025 |
|
Comp Negotiation Fundamentals for Tech Sales
|
Apr 30, 2025 |
|
Key Mindset Shifts for Long-Term Success in Tech Sales
|
Apr 24, 2025 |
|
Are You Staying Competitive in Deals?
|
Apr 16, 2025 |
|
Using AI to Build The "R" in your CRM with Rachit Kataria of Centralize
|
Apr 10, 2025 |
|
Dealing with Uncertain Times as a Tech Seller (& I Need YOUR Feedback)
|
Apr 06, 2025 |
|
Here's How I Engage the Execs at My Top Accounts
|
Apr 04, 2025 |
|
Why It's Important to Find Your Niche in Tech Sales
|
Mar 29, 2025 |
|
Improving Your Close Rate & Driving Predictability in Your Pipeline & Deals
|
Mar 24, 2025 |
|
How to Pick a Winning Startup as a Seller
|
Mar 20, 2025 |
|
How to Ace Sales Interviews & Be the Top Candidate
|
Mar 06, 2025 |
|
Lessons from the Startup Trenches with Amanda Crooks of BlinkMetrics
|
Feb 26, 2025 |
|
7 Tips for Getting the Most Out of Your Meeting Recording Tool
|
Feb 19, 2025 |
|
Winning an Electric Car as a Sales Spiff and Other Crazy Career Stories with Chris Dankowski
|
Feb 12, 2025 |
|
Why Your Buyers Don't Take You Seriously + Show Update & Re-Intro
|
Feb 07, 2025 |
|
Outcome of 7-Figure Deal: Increase in Customer Stock Price - Pod Swap with How the Deal Was Done
|
Jan 16, 2025 |
|
Building Your Professional Network Via Slack with Kaela Altman of Salesforce, Salesblazers
|
Jan 06, 2025 |
|
Becoming a Subject Matter Expert in Sales with Morgan J. Ingram
|
Dec 19, 2024 |
|
How to Use AI to Hit Your Goal in 2025 with Dustin Beaudoin of ChatAE
|
Dec 12, 2024 |
|
The Sales Ops Path to CRO with Kevin McIntyre of Dealfront
|
Nov 21, 2024 |
|
The Work Before the Work, Learning the Habits of Elite Sellers with Paul M. Caffrey
|
Nov 15, 2024 |
|
Finding Your Edge in Sales with Jeb Blount of Sales Gravy
|
Nov 04, 2024 |
|
Building a Process-Driven Sales Team with Mike Simmons of Catalyst
|
Oct 23, 2024 |
|
Key Skills for Selling in a Startup with Egan Montgomery of Backstroke
|
Oct 18, 2024 |
|
A Founder's Guide to Career Growth & Transformation with Corey Kossack of Aspireship
|
Oct 07, 2024 |
|
Elevating Your Sales Process with Automation with Shimmy Savitsky of Esek
|
Oct 01, 2024 |
|
How to Start Building an Online Brand (That Actually Helps You Sell) - Live Replay from SP Virtual Meetup
|
Sep 21, 2024 |
|
Ideas for Staying Motivated in Sales & Humanizing Sales Metrics with Phil Putnam
|
Sep 19, 2024 |
|
From AE to CEO & Driving Sales with Personalized Gifts with Kris Rudeegraap of Sendoso
|
Sep 12, 2024 |
|
Mastering Comp Negotiation with Devon Hennig
|
Sep 05, 2024 |
|
Remote Work, AI, and Predictions on the Future of Sales with Scott Leese
|
Aug 29, 2024 |
|
Understanding: Comp Plans, PIPs, Severance, Equity Grants & Commission Issues with Dan Goodman
|
Aug 21, 2024 |
|
Closing More Complex Deals with Krysten Conner
|
Aug 13, 2024 |
|
Growing Your Exposure with GenAI with Joe Apfelbaum of evyAI
|
Aug 07, 2024 |
|
Finding Balance & Community in Sales with JC Pollard of Holistic Sales Co/Gong
|
Jul 31, 2024 |
|
1080s, 1099s and Balancing Sales Leadership as a Competitive Snowboarder with Jayden Belcher
|
Jul 24, 2024 |
|
Why Sales Skills Are Life Skills with Shane Jamison
|
Jul 17, 2024 |
|
Building an Audience on LinkedIn & Going from Seller to Co-Founder with Sarah Brazier of Dimmo
|
Jul 09, 2024 |
|
Driving Execution Excellence for Sales with Ross Rich of Accord
|
Jun 27, 2024 |
|
These Are the Tools We Can't Live Without As Sellers
|
Jun 15, 2024 |
|
From Copywriting to Closing with Mor Assouline
|
Jun 11, 2024 |
|
The Seller's Journey, Psychology Sales & Building a Sales Coaching Bot with Richard Harris
|
May 30, 2024 |
|
10 Things That Might Be Costing You Deals
|
May 26, 2024 |
|
Our Must-Read Books for Sellers
|
May 22, 2024 |
|
Stealing the Sales Playbooks of the Top 0.01% with Chris Orlob of pclub.io
|
May 14, 2024 |
|
Improving Your Pitch with a Story
|
May 06, 2024 |
|
From Valet to VP of Sales with Colin Specter of Orum
|
Apr 25, 2024 |
|
Innovative Pipe Generation Ideas to Implement ASAP with Tom Slocum of The SD Lab
|
Apr 16, 2024 |
|
Building a Flywheel Business & Going to Market with an Affiliate Sales Model with Ramon Berrios of Castmagic
|
Apr 09, 2024 |
|
The Secret to Selling with Video on LinkedIn with Danny DelVecchio
|
Apr 02, 2024 |
|
Build What Sells. Sell What you Built with Derek Osgood of Ignition
|
Mar 25, 2024 |
|
Tips for Running Great Demos, Fighting Customer Churn & Building High Performing Teams with Barry Klein of Talroo
|
Mar 14, 2024 |
|
Landing on your Feet After a Layoff
|
Mar 11, 2024 |
|
Bootstrapping a Startup & Scaling Sales with AI with Brad Scruggs of ZyraTalk
|
Feb 21, 2024 |
|
Anyone, Not Everyone & Escaping Founder-Led Sales with Corey Quinn
|
Feb 13, 2024 |
|
From Grassroots to Greatness, Community Led Growth, Building Boast.AI & Traction & Living in Dubai with Lloyed Lobo
|
Feb 02, 2024 |
|
Brainstorming Ideas for Growing Your Network & Influence on LinkedIn
|
Jan 30, 2024 |
|
Going From SDR to AE in Only 5 Months & The Best Tacos in Texas with Tony Gomez of WhatConverts
|
Jan 23, 2024 |
|
How to Get the Most Out of Trade Shows, Meet-Ups & In-Person Events
|
Jan 19, 2024 |
|
Growing a Bootstrapped SaaS from $0-$20M Using Content & Social Selling with Guillaume Moubeche of lemlist
|
Jan 16, 2024 |
|
Here's Our Top 3 Sources for Generating Pipeline This Year
|
Jan 13, 2024 |
|
Entrepreneurship, Side Hustles & How Sellers Can Start Building Long-Term Wealth
|
Jan 09, 2024 |
|
Can You Survive as an Average Sales Performer?
|
Jan 09, 2024 |
|
Pod "Re-Brand," New Co-Host (Chase Barmore) & The Time I Met Tim Ferris
|
Jan 02, 2024 |
|
10 (Unconventional) Things I Plan to Do Next Year to Level Up
|
Dec 13, 2023 |
|
Selling in Startups & Building a Co-Selling Community for High Performing Sellers with Vince Beese of Sales HQ
|
Nov 29, 2023 |
|
Improving Pipeline & Revenue by Connecting your CRM (in 60 seconds) with LinkedIn with David Chevalier of Surfe
|
Nov 16, 2023 |
|
Using Forcing Functions to Drive Results
|
Oct 30, 2023 |
|
Filling Your Funnel & Building a Great Sales Career with Gabe Lullo of Alleyoop
|
Oct 19, 2023 |
|
An Important Factor for Success That Nobody Really Talks About
|
Oct 11, 2023 |
|
Leveling Up with Your Sales Stack (Outreach Unleash Teaser)
|
Oct 02, 2023 |
|
Stop Losing Deals When Your Not in the Room with Nate Nasralla of Fluint
|
Sep 08, 2023 |
|
Re-Thinking Pipeline Generation with Todd Busler of Champify
|
Aug 24, 2023 |
|
Selling to Developers, Building Strong Champions & Company-Wide Pipeline Generation with Dustin Beaudoin of Airplane
|
Aug 21, 2023 |
|
Creating Outbound Sequences That Actually Work with David Breshears
|
Aug 17, 2023 |
|
SaaS Sales Side Hustles... Should You Start One?
|
Aug 10, 2023 |
|
Exploring the Indie Tech Stack with James Urie of Close
|
Aug 03, 2023 |
|
Story Time: When I Closed My First $100K Deal
|
Jul 21, 2023 |
|
Becoming a Category Expert & Humanizing Your Sales Cycles with Andy Teipen
|
Jul 20, 2023 |
|
Part III - Closing Your First (Or Next) $100K+ SaaS Deal
|
Jul 12, 2023 |
|
Part II - Closing Your First (Or Next) $100K+ SaaS Deal
|
Jul 07, 2023 |
|
Part I - Closing Your First (Or Next) $100K+ SaaS Deal
|
Jul 05, 2023 |
|
Building the Future of Manufacturing with SaaS with Renan Devillieres of OSS Ventures
|
Jun 28, 2023 |
|
Growing Your Online Network and the Future of Selling with Scott Leese
|
Jun 21, 2023 |
|
A Day in the Life of a SaaS CEO with Jennifer Smith of Scribe
|
Jun 12, 2023 |
|
Steal My Value Drivers Template to Improve Your Messaging & Pitch
|
Jun 09, 2023 |
|
The Intersection of AI & Sales with Wissam Tabbara of Truebase
|
Jun 05, 2023 |
|
How to Find the Right Path in Your Sales Career with Chris Dankowski
|
May 31, 2023 |
|
Proposing Next Steps and Implementing a Mutual Action Plan to Improve your Odds of Closing the Deal
|
May 26, 2023 |
|
Are You Selling a Vitamin or a Painkiller?
|
May 19, 2023 |
|
How to Self-Source the Right Buyer at the Right Time with the Right Message with Jamie Shanks of Pipeline Signals
|
May 11, 2023 |
|
From Personal Banker to SaaS CEO, Customer Led Growth & Sales Automation Insights with Rafael Figueroa of Overloop
|
May 04, 2023 |
|
Building & Scaling Profitable SaaS & Services Companies with Phil Alves of DevStats/DevSquad
|
Apr 27, 2023 |
|
How to Negotiate a Signing Bonus for Your Next Role
|
Apr 25, 2023 |
|
10 SaaS Sales Predictions
|
Apr 14, 2023 |
|
Networking, Negotiating & Winning SaaS Deals Quickly with Chase Barmore of WhatConverts
|
Apr 06, 2023 |
|
How I Nurture Prospects Without Sending Annoying “Check-in” Emails
|
Apr 01, 2023 |
|
A Recruiter's Perspective on Growth, Interviewing & Evaluating Opportunities with Christine Kull
|
Mar 22, 2023 |
|
December Recap, New Year & Updates
|
Jan 09, 2023 |
|
Making an Impact as an Early Sales Hire
|
Nov 30, 2022 |
|
4 Tips to Recession-Proof Your Message & Pitch
|
Nov 18, 2022 |
|
Retiring the Hawaiian Shirt Headshot, Ratings & Reviews, Slack Channel & Other Updates
|
Nov 18, 2022 |
|
Sell with Swagger with Tim Zielinski of Dynatrace
|
Nov 03, 2022 |
|
How Sellers Can Improve Their Executive Presence
|
Nov 03, 2022 |
|
Why You Shouldn't Let Your Tech Career Destroy Your Health
|
Oct 31, 2022 |
|
Challenger Selling? In this Economy?!? with Jen Allen-Knuth
|
Oct 24, 2022 |
|
Key Insights from a Sales Enablement Leader with Lauren Flannery of Whoop
|
Oct 13, 2022 |
|
Common Reasons Your Deals Stall & How You Can Fix It
|
Sep 24, 2022 |
|
Improving Outbound & Growing Your Sales Pipeline with Christian Banach
|
Sep 14, 2022 |
|
From Entrepreneur & Small Business Owner to High Performing SaaS Seller with Chase Barmore of WhatConverts
|
Sep 01, 2022 |
|
Prospecting & Prioritizing Mental Health, Mindset, and Wellness from an SDR Turned AE with Anthony Natoli
|
Aug 24, 2022 |
|
You're Probably More Valuable Than You Think...
|
Aug 12, 2022 |
|
Sales Secrets from a $100M Sales Rep with Brandon Bornancin of Seamless.AI
|
Jul 28, 2022 |
|
The Importance of Being Brief in SaaS Sales
|
Jul 07, 2022 |
|
Layoffs in Tech & What to Do If You're Impacted
|
Jun 09, 2022 |
|
Do You Have a Highlight Reel for Your SaaS Sales Career?
|
May 20, 2022 |
|
A Prospecting Campaign Idea to Help You Get Intro'd To The Right Stakeholders
|
May 13, 2022 |
|
What Happens If I Miss My Quota?
|
Apr 29, 2022 |
|
The Secret to Scaling SaaS Companies From Someone Who's Done It Many Times Over with Patrick Parker of SaaS Partners
|
Apr 14, 2022 |
|
Announcement! - First Ever SSP Happy Hour & Meetup in Austin, Texas
|
Mar 30, 2022 |
|
Knowing Your On Track in Your SaaS Sales Journey
|
Mar 24, 2022 |
|
Data Security, Compliance & Selling to Technical Buyers with Girish Redekar of Sprinto
|
Mar 17, 2022 |
|
How to Transform Your Mindset, Manage Stress, Anxiety & Addiction & Become an Elite Seller with Ian Koniak
|
Mar 04, 2022 |
|
Breaking Down Common Acronyms in the SaaS Business (While Drinking Tequila)
|
Feb 19, 2022 |
|
A Stanford Ph.D's Approach to Selling & The Value-Driven Growth Methodology with Brent Keltner of Winalytics
|
Feb 14, 2022 |
|
A Simple Formula to Estimate the Annual Revenue & Burn Rate of any SaaS Startup
|
Feb 08, 2022 |
|
Mastering Your Pitch with Rajiv 'RajNATION' Nathan
|
Feb 03, 2022 |
|
7 Steps to 7 Figures in SaaS Sales with Brandon Fluharty
|
Jan 30, 2022 |
|
Knowing Your Tech Stack, Marketplace & Transitioning from Contributor to Leader with Asa Hochhauser of McGaw.io
|
Jan 20, 2022 |
|
The Simple Cadence I'm Using for my Prospecting
|
Jan 20, 2022 |
|
Sales & Prospecting Insights from a Lawyer Turned SaaS Founder with Andy Cabasso of Postaga
|
Jan 11, 2022 |
|
Quick Time Management Tip for SaaS Sellers
|
Jan 08, 2022 |
|
Career Transitions, Startups, Research & Streamlining Results with David Nakano of Airkit
|
Jan 06, 2022 |
|
Pt. III Accelerating Your SaaS Selling Results & Career in 2022 - Ideas for Owning Your Career Path
|
Dec 31, 2021 |
|
Pt. II Accelerating Your SaaS Selling Results & Career in 2022 - Breaking into SaaS Sales
|
Dec 30, 2021 |
|
Pt. I Accelerating Your SaaS Selling Results & Career in 2022 - Earning A Record W2
|
Dec 28, 2021 |
|
How to Sell Without Selling Out with Andy Paul
|
Dec 21, 2021 |
|
My Top 10 Must-Read Books for Business & Sales
|
Dec 01, 2021 |
|
From Bankrupt Small Business Owner to Top SaaS Seller with Chris Dankowski of Sapper Consulting
|
Nov 17, 2021 |
|
How to Master a Salary Negotiation in SaaS
|
Nov 10, 2021 |
|
Managing Your SaaS Sales Career with Christine Rogers of Aspireship
|
Oct 29, 2021 |
|
Meeting Your Prospects Where They Are Using Social Selling with Ryann Dowdy of Social Sellers Academy
|
Oct 26, 2021 |
|
5 Tips for Better Discovery Conversations
|
Oct 24, 2021 |
|
Sales Transformation, Podcasting & Startup Sales with Collin Mitchell of Salescast
|
Oct 20, 2021 |
|
How to Find Great Opportunities in SaaS Sales with Amanda Jones
|
Oct 14, 2021 |
|
Deconstructing the Challenger Sale with Jennifer Allen-Knuth of Challenger
|
Oct 06, 2021 |
|
Authentic Persuasion & Going From Order Taker to Quota Breaker with Jason Cutter
|
Oct 01, 2021 |
|
How to Be Focused, Live Great AND Make 7 Figures in SaaS Sales with Brandon Fluharty
|
Sep 20, 2021 |
|
Death to Fluff in Sales & the Mic Drop Method for Cold Calling with Belal Batrawy
|
Sep 07, 2021 |
|
Sales Lessons from a Veteran Entrepreneur with Patrick Baynes of NerdWise
|
Sep 01, 2021 |
|
How to Maintain a Positive Mindset When Things Aren’t Going Well
|
Aug 21, 2021 |
|
Using LinkedIn Sales Navigator to Build Credibility, Find Buyers & Create Org Charts
|
Aug 11, 2021 |
|
On Being a Rainmaker, "LinkedIn Rapper" & Highly Competitive Seller with Jaime Safianow of Quantum Metric
|
Aug 02, 2021 |
|
6-Figure Close Plan (Program Launch Announcement)
|
Aug 02, 2021 |
|
Is SaaS Sales a Career or a Lifestyle?
|
Jul 27, 2021 |
|
Mastering The Cold Call With Chris Beall of ConnectAndSell
|
Jul 07, 2021 |
|
Developing Winning Habits & Using Your Resources to Find Success in Software Sales with Scott Milener of IntroSnap
|
Jun 25, 2021 |
|
5 Things to Look For When Interviewing for your Next SaaS Sales Role
|
Jun 05, 2021 |
|
What Sales Can Learn from Special Operations Forces (SOF) with John Wood
|
May 19, 2021 |
|
4 Things I'm Proud of in My SaaS Sales Journey
|
May 12, 2021 |
|
3 Things I Would Have Done Differently In My SaaS Sales Journey
|
Apr 30, 2021 |
|
How Having a "Close Plan" Will Help You Improve Forecasting & Conversions
|
Apr 07, 2021 |
|
Podcast Update
|
Mar 03, 2021 |
|
The Fundamentals of SaaS Selling with Jeroen Corthout of Salesflare
|
Feb 18, 2021 |
|
The Number One Question To Ask When Discussing Pricing
|
Feb 08, 2021 |
|
The Secret to Closing $10MM+ Mega Software Deals with Jamal Reimer
|
Feb 01, 2021 |
|
"Can You Send Me Some More Info?"
|
Jan 27, 2021 |
|
How to Double Your Income This Year In Software Sales with Ian Agard of Clio & Grind
|
Jan 16, 2021 |
|
On Succeeding as the First Sales Hire with Luke Bivens of Gatsby
|
Jan 05, 2021 |
|
Finding Your First Opportunity in SaaS Sales - Pt. III
|
Jan 05, 2021 |
|
Finding Your First Opportunity in SaaS Sales - Pt. II
|
Dec 19, 2020 |
|
Finding Your First Opportunity in SaaS Sales - Pt. I
|
Dec 09, 2020 |
|
Getting After It with Leigh Kindley of 6sense
|
Nov 28, 2020 |
|
Breaking Up (Disqualifying) Prospects That Aren't a Fit
|
Nov 20, 2020 |
|
How to Multi-Thread Your Deals
|
Nov 19, 2020 |
|
Being Authentic and Asking the Right Questions with Zachary Ballenger of Casted
|
Nov 04, 2020 |
|
Call CFOs
|
Oct 22, 2020 |
|
How to Make "No" Work for You
|
Oct 09, 2020 |
|
How to Win Big Deals and Influence Customers with Dustin Brown of Outreach.io
|
Oct 08, 2020 |
|
Take on Complexity for your Customers
|
Oct 02, 2020 |
|
Do the Hard Thing
|
Sep 29, 2020 |
|
How to Ramp 80% Faster with Amanda Jones of Chorus.ai
|
Sep 25, 2020 |
|
Trailer
|
Sep 20, 2020 |