PODCAST · business
Sales Players
by Jesse Woodbury
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.
Episodes
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Making the Most of Your Tech Sales Career
Jesse shares lessons on making the most of the tech sales career opportunity. SPONSORS: ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership EPISODE LINKS: • 20 Questions Download:...
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Lessons on Building a Personal Brand from 5 Years of Podcasting
Lessons on (personal) brand building from 5 years of hosting this podcast. SPONSORS: ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership EPISODE LINKS: • 20 Questions Download:...
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20 Questions I Use to Stress-Test My Deals
Jesse shares 20 go-to questions for introducing friction in your deals. SPONSORS: ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership EPISODE LINKS: • 20 Questions Download:...
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What I’m Hearing: Sales Trends Shaping Tech in 2025
Jesse shares insights on trends he's hearing about from conversations with sales leaders, founders, and recruiters etc. SPONSORS: ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership EPISODE LINKS: • Schedule 1:1 Coaching...
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How I Re-Engage Closed-Lost Opportunities
Jesse shares his approach to building pipeline from the closed-lost deals in your territory. SPONSORS: ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership EPISODE LINKS: • Re-engagement Email Template:...
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5 Habits That Close More Deals
Jesse shares five simple but powerful habits that increase your chances of closing more deals. SPONSORS: ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership EPISODE LINKS: • Aug '25 Coaching Promo ($99 Sessions) Book at:...
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Your Network Is Doing More for Your Sales Career Than You Think
Jesse shares ideas for getting yourself out there and building your network. SPONSORS: ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership SPONSORS: ChatAE (AI Account Planning):...
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5 Ideas for Turning Your Sales Skills Into Extra Income
Jesse shares five side hustles that B2B sellers can launch without leaving their day job. He walks through ideas he’s personally tested to turn sales skills into extra income while working full-time in tech sales. SPONSORS: ChatAE (AI Account Planning):...
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Why Reps Are Ditching Managers for AI Roleplay with Sriharsha (Sai) Guduguntla of Hyperbound
Sriharsha (Sai) Guduguntla is the Co-Founder of Hyperbound, an AI Sales Coach. He joins Jesse to share insights into how sellers can use AI to improve their craft. SPONSORS: ChatAE (AI Account Planning):...
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The Metrics That Matter Most in Tech Sales
Jesse breaks down the exact numbers he tracks to stay on target and outperform quota. SPONSORS: ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership EPISODE LINKS: • 1:1 Coaching Intro:...
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What My Former Sales Leader Taught Me About Red Zone Selling with Vince Beese
Jesse sits down with his former sales leader Vince Beese, the only exec he’s ever seen cold call procurement to get a deal done. They break down Vince’s new book Red Zone Selling, including tactical plays for managing late-stage deals, building mutual action plans that actually work, and why...
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20 Sales Plays I Run When Nothing Else Is Working
Jesse shares 20 proven sales plays he turns to when deals stall, pipeline dries up, or nothing seems to be working. These are high-leverage, momentum-building activities that have helped him bounce back from slumps and close big deals. SPONSORS: ChatAE (AI Account Planning):...
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Building Financial Security as a Tech Seller
Jesse (who is not giving financial or investment advice) shares why tech sellers have a huge advantage when it comes to building wealth and financial security. He shares a few things you can do to develop financial security which will enhance your selling career. SPONSORS: ChatAE (AI Account...
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The Anonymous Tech Seller Who Built a 6-Figure Side Hustle with "Fidel Cache Flow"
Jesse sits down with "Fidel Cache Flow," an anonymous tech seller who’s built a cult following on Sales Twitter with unfiltered takes on career growth, wifi money, and escaping the W2 grind. Fidel runs Desperados, a fast-growing private community for sellers looking to build income beyond quota.…
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23 Absolute Truths About Enterprise Selling
Jesse breaks down 23 hard-earned truths about enterprise sales that every seller should know SPONSORS: ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership EPISODE LINKS: • Read the 23 Truths:...
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What Top Tech Sales Candidates Do Differently
The best candidates don’t just show up, they sell themselves at every step. In this episode, Jesse shares the high-leverage interview plays that get offers in today’s brutal job market. SPONSORS: ChatAE (AI Account Planning):...
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Top Tech Sellers Share These 10 Traits
Jesse breaks down the 10 traits that separate good reps from top-performing enterprise and mid-market sellers. After a decade in tech sales and five years interviewing the best in the game, he shares what it really takes to sell at the highest level. SPONSORS: ChatAE (AI Account Planning):...
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What I Learned (the Hard Way) as a Founding AE
Jesse shares the unfiltered story of his time as the founding AE at a seed-stage startup. From landing the role on a mountain bike trail to building sales ops from scratch, it's a raw look at what early-stage startup life is really like. SPONSORS: ChatAE (AI Account Planning):...
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This Is Exactly How I Approach Cold Calls Every Day
Jesse breaks down the exact cold call routine he uses daily to drive pipeline. SPONSORS: ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership EPISODE LINKS: • Want to get better at cold calls? Book FREE 1:1 Coaching Intro...
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Want Bigger Deals? Learn the Product
Jesse reminds sellers why understanding the product matters, especially when selling to IT buyers. SPONSORS: ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership EPISODE LINKS: • Book FREE 1:1 Coaching Intro with Jesse:...
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A Week in My Life: Tech Sales, Family, Fitness & Side Projects
Jesse shares a real-life look at how he juggles tech sales, content creation, fitness, and family life each week. SPONSORS: ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership EPISODE LINKS: • Book FREE 1:1 Coaching Intro...
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Why You're Still an SDR (and What to Do About It)
Jesse shares real strategies for SDRs looking to break into AE roles, drawing from his own journey from SDR > SDR Leader > Enterprise AE. SPONSORS: ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership EPISODE LINKS: • Book...
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Why You Should Hold Off on Going Fully Remote in Your Career
Jesse gives his take on why you should consider spending the first few years of your career in an office. SPONSORS: ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership EPISODE LINKS: • Book FREE 1:1 Coaching Intro with...
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Comp Negotiation Fundamentals for Tech Sales
Jesse shares his basic process for negotiating compensation as a tech seller. SPONSORS: ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership EPISODE LINKS: • Book FREE 1:1 Coaching Intro with Jesse:...
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Key Mindset Shifts for Long-Term Success in Tech Sales
Jesse talks about mindset shifts sellers can embrace for long-term success. SPONSORS: ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership EPISODE LINKS: • Pre-Order Commission Impossible! -...
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Are You Staying Competitive in Deals?
Jesse shares ideas for how you can become a more fierce competitor in your deals. SPONSORS: ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership EPISODE LINKS: • Mutual Action Plan:...
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Using AI to Build The "R" in your CRM with Rachit Kataria of Centralize
Rachit Kataria is the Co-Founder & CEO of Centralize (https://www.usecentralize.com/) an all-in-one deal collaboration platform for enterprise revenue teams backed by Y Combinator. In this episode, Rachit shares his career story, the origins of Centralize, and the AI opportunity for Enterprise...
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Dealing with Uncertain Times as a Tech Seller (& I Need YOUR Feedback)
Jesse shares how he is planning to navigate the uncertain times ahead and asks for feedback on what direction to take the show. Please reach out on Slack, InMail, or email [email protected] to share: #1 What keeps you coming back to the show? #2 What topics would you like to hear more about?...
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Here's How I Engage the Execs at My Top Accounts
Jesse shares the 10k play for developing a PoV when reaching out to executives at public companies. SPONSORS: ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership EPISODE LINKS: • Book FREE 1:1 Coaching Intro with Jesse:...
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Why It's Important to Find Your Niche in Tech Sales
Jesse shares thoughts on the current state of the market and some insights on the importance of finding a niche or specialization in your tech sales career. SPONSORS: ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership...
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Improving Your Close Rate & Driving Predictability in Your Pipeline & Deals
Jesse shares a checklist of ideas for de-risking your deals to increase your close rate and drive more predictability in your pipeline and deals. SPONSORS: ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership EPISODE…
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How to Pick a Winning Startup as a Seller
Jesse shares some ideas for choosing a winning startup by drawing from his own experience working in early startups as a seller. SPONSORS: ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership EPISODE LINKS: • Books...
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How to Ace Sales Interviews & Be the Top Candidate
Jesse shares insights on the current state of tech sales hiring with ideas for how to ace your next interview. SPONSORS: ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership EPISODE LINKS: • Book FREE 1:1 Coaching Intro…
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Lessons from the Startup Trenches with Amanda Crooks of BlinkMetrics
Amanda Crooks is the Founding Director of BlinkMetrics. In this episode, she joins Jesse to share lessons from selling software in a bootstrapped startup. SPONSORS: ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership...
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7 Tips for Getting the Most Out of Your Meeting Recording Tool
Jesse shares some tips for getting the most out of your sales meeting recordings tool (Gong, Chorus etc.) SPONSORS: ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership EPISODE LINKS: • Get Fathom: Get Fathom:...
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Winning an Electric Car as a Sales Spiff and Other Crazy Career Stories with Chris Dankowski
Chris Dankowski is a Sales Strategy Consultant and Coach to Sellers and Founders in tech. Based in Austin, Texas, Chris has previously sold at top companies like: Evernote, Outreach and HubSpot. In this episode, Chris shares insights on managing your tech sales career. SPONSORS: ChatAE (AI…
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Why Your Buyers Don't Take You Seriously + Show Update & Re-Intro
Jesse shares an update on the future of Sales Players, re-introduces his background and shares an important mindset shift that will help your buyers take you more seriously. SPONSORS: ChatAE (AI Account Planning):...
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Outcome of 7-Figure Deal: Increase in Customer Stock Price - Pod Swap with How the Deal Was Done
*Pod Swap - Jesse's interview on the How the Deal Was Done podcast: Jesse Woodbury shares his journey of converting a small proof of concept into a seven-figure deal with a B2C Home Services Company. A deal so impactful it raised the buying company’s share price. This deal is a perfect example of...
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Building Your Professional Network Via Slack with Kaela Altman of Salesforce, Salesblazers
Kaela Altman is the Community Manager for the Salesforce, Salesblazers sales networking community. Based in New York, she brings 15+ years of building, managing, and growing communities for enterprise tech. She joins the Sales Players to share details about growing and managing the Salesblazers...
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Becoming a Subject Matter Expert in Sales with Morgan J. Ingram
Morgan J. Ingram is the Founder & CEO of AMP Creative. Morgan is a force to be reckoned with in the B2B Sales Community. He initially gained traction as the creator and host of The SDR Chronicles and has since gone on to build an amazing career as a subject matter expert, keynote speaker and...
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How to Use AI to Hit Your Goal in 2025 with Dustin Beaudoin of ChatAE
Dustin Beaudoin is the Founder of ChatAE, a copilot built for pre- and post-call tasks. Built to prep for calls, write recap emails, and plan next steps while coaching you to become an elite seller. Dustin joins SP to share ideas for leveraging AI in your sales process. SPONSORS: • Leadfeeder…
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The Sales Ops Path to CRO with Kevin McIntyre of Dealfront
Kevin McIntyre is the CRO of Dealfront. In this episode he joins the Sales Players to share insights from his career journey to CRO. SPONSORS: • Leadfeeder (Turn Page Views into Pipeline) - https://leadfeeder.partnerlinks.io/rsscjriylqgb this link for an extended, 21-day free trial •...
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The Work Before the Work, Learning the Habits of Elite Sellers with Paul M. Caffrey
Paul M. Caffrey is a Dublin-based Author, Speaker & Sales Performance Coach. He joins the Sales Players to share insights from his work as an AE coach and author of the book: The Work Before the Work: The Hidden Habits Elite Sales Professionals Use to Outperform the Competition. SPONSORS: •...
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Finding Your Edge in Sales with Jeb Blount of Sales Gravy
Jeb Blount is the author of 15 books, including Fanatical Prospecting, a staple in the modern tech sales world. Jeb is a coach and advisor and founded Sales Gravy to help sales organizations, sales leaders, and sales professionals sell more. Jeb joins the Sales Players to share ideas for…
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Building a Process-Driven Sales Team with Mike Simmons of Catalyst
Mike Simmons is the Founder of Catalyst A.C.T.S which helps technical SaaS founders and team leaders scale their organizations from $2M - $80M ARR using design thinking. Mike is based in Phoenix, AZ and joins the Sales Players to share insights around process, people, communication and…
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Key Skills for Selling in a Startup with Egan Montgomery of Backstroke
Egan Montgomery is the Co-Founder of Backstroke, a GenAI email platform marketers. Based in Indy, Egan joins the Sales Players to share lessons learned from his career journey from Intern to Founder. SPONSORS: • Leadfeeder (Turn Page Views into Pipeline) -...
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A Founder's Guide to Career Growth & Transformation with Corey Kossack of Aspireship
Corey Kossack is the Founder & CEO of Aspireship a career acceleration platform built for the modern workforce. Corey's based in Scottsdale, Arizona and he joins the Sales Players to share his perspective on the current state of the job market while sharing lessons on career growth, transition…
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Elevating Your Sales Process with Automation with Shimmy Savitsky of Esek
Shimmy Savitsky is the Founder of Esek, an automation consulting agency that specializes in helping salespeople. Shimmy joins the Sales Players to share some ideas for incorporating more automation into the sales process. SPONSORS: • Leadfeeder (Turn Page Views into Pipeline) -...
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How to Start Building an Online Brand (That Actually Helps You Sell) - Live Replay from SP Virtual Meetup
A replay from our most recent SP virtual meetup. Join us in Slack to get notified about the next one: https://www.launchpass.com/saas_sales_players SPONSORS: • Leadfeeder (Turn Page Views into Pipeline) - https://leadfeeder.partnerlinks.io/rsscjriylqgb - SP fans use this link for an…
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Ideas for Staying Motivated in Sales & Humanizing Sales Metrics with Phil Putnam
Phil Putnam is a speaker, author, coach & workshop leader helping leaders get top team performance and extend employee tenure. He joins the Sales Players to share insights into staying motivated in sales. SPONSORS: • Leadfeeder (Turn Page Views into Pipeline) -...
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ABOUT THIS SHOW
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.
HOSTED BY
Jesse Woodbury
CATEGORIES
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Frequently Asked Questions
How many episodes does Sales Players have?
Sales Players currently has 205 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is Sales Players about?
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...
How often does Sales Players release new episodes?
Sales Players publishes regularly with 205 episodes available. Check the episode list for the typical release schedule.
Where can I listen to Sales Players?
You can listen to Sales Players on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts Sales Players?
Sales Players is created and hosted by Jesse Woodbury.
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