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 enterprise sales is more like football than most reps realize. If you're selling big deals in a competitive market, this one's a masterclass. EPISODE LINKS: • Connect with Vince: https://www.linkedin.com/in...
Jun 26, 2025•49 min
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. EPISODE LINKS: • https://www.salesplayers.co/posts/20-high-leverage-sales-activities CONNECT WITH JESSE: • LinkedIn: https://www.linkedin.com/in/jessewoodbury/ • Website: https://jessewoodbury.com/ HELP GROW SP: • Join Sales Players Slack Community: https://www.la...
Jun 21, 2025•9 min
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. CONNECT WITH JESSE: • LinkedIn: https://www.linkedin.com/in/jessewoodbury/ • Website: https://jessewoodbury.com/ HELP GROW SP: • Join Sales Players Slack Community: https://www.launchpass.com/saas_sales_players/free • Get a weekly email...
Jun 14, 2025•26 min
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. In this episode, they dive into contract stacking, virtual assistants, building while employed, and why aiming for #1 on the leaderboard might be the wrong game. EPISODE LINKS: • Follow: https://x.com...
Jun 11, 2025•39 min
Jesse breaks down 23 hard-earned truths about enterprise sales that every seller should know SPONSORS: • ZoomInfo (The GTM Intelligence Platform) - Link for SP extended trial offer: https://try.zoominfo.com/sp EPISODE LINKS: • Read the 23 Truths: https://www.salesplayers.co/posts/23-absolute-truths-about-enterprise-selling • Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-coaching-overview CONNECT WITH JESSE: • LinkedIn: https://www.linkedin.com/in/jessewoodbury/ ...
Jun 09, 2025•4 min
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: • ZoomInfo (The GTM Intelligence Platform) - Link for SP extended trial offer: https://try.zoominfo.com/sp EPISODE LINKS: • Join the FREE Sales Players Slack Community: https://www.launchpass.com/saas_sales_players/free • Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-co...
Jun 06, 2025•10 min
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: • ZoomInfo (The GTM Intelligence Platform) - Link for SP extended trial offer: https://try.zoominfo.com/sp EPISODE LINKS: • Read: https://www.salesplayers.co/posts/top-tech-sellers-share-these-10-traits • Book FREE 1:1 Coaching Intro with ...
Jun 04, 2025•4 min
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: • ZoomInfo (The GTM Intelligence Platform) - Link for SP extended trial offer: https://try.zoominfo.com/sp EPISODE LINKS: • Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-coaching-overview CONNECT WITH JESSE: • LinkedIn...
May 28, 2025•20 min
Jesse breaks down the exact cold call routine he uses daily to drive pipeline. SPONSORS: • ZoomInfo (The GTM Intelligence Platform) - Link for SP extended trial offer: https://try.zoominfo.com/sp EPISODE LINKS: • Want to get better at cold calls? Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-coaching-overview CONNECT WITH JESSE: • LinkedIn: https://www.linkedin.com/in/jessewoodbury/ • Website: https://jessewoodbury.com/ HELP GROW SP: • Join Sales Players Slack C...
May 21, 2025•10 min
Jesse reminds sellers why understanding the product matters, especially when selling to IT buyers. SPONSORS: • Surfe (LinkedIn Prospecting Streamlined) - SP promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury EPISODE LINKS: • Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-coaching-overview CONNECT WITH JESSE: • LinkedIn: https://www.linkedin.com/in/jessewoodbury/ • Website: https://jessewoodbury.com/ HELP GROW SP: • Join Sales Players Slack Community: https:...
May 15, 2025•10 min
Jesse shares a real-life look at how he juggles tech sales, content creation, fitness, and family life each week. SPONSORS: • Surfe (LinkedIn Prospecting Streamlined) - SP promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury EPISODE LINKS: • Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-coaching-overview CONNECT WITH JESSE: • LinkedIn: https://www.linkedin.com/in/jessewoodbury/ • Website: https://jessewoodbury.com/ HELP GROW SP: • Join Sales Players Slack Co...
May 10, 2025•18 min
Jesse shares real strategies for SDRs looking to break into AE roles, drawing from his own journey from SDR > SDR Leader > Enterprise AE. SPONSORS: • Surfe (LinkedIn Prospecting Streamlined) - SP promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury EPISODE LINKS: • Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-coaching-overview CONNECT WITH JESSE: • LinkedIn: https://www.linkedin.com/in/jessewoodbury/ • Website: https://jessewoodbury.com/ HELP GROW SP:...
May 07, 2025•20 min
Jesse gives his take on why you should consider spending the first few years of your career in an office. SPONSORS: • Pre-Order Commission Impossible! - https://www.salesplayers.co/products/ci EPISODE LINKS: • Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-coaching-overview CONNECT WITH JESSE: • LinkedIn: https://www.linkedin.com/in/jessewoodbury/ • Website: https://jessewoodbury.com/ HELP GROW SP: • Join Sales Players Slack Community: https://www.launchpass.com/...
May 01, 2025•7 min
Jesse shares his basic process for negotiating compensation as a tech seller. SPONSORS: • Pre-Order Commission Impossible! - https://www.salesplayers.co/products/ci EPISODE LINKS: • Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-coaching-overview CONNECT WITH JESSE: • LinkedIn: https://www.linkedin.com/in/jessewoodbury/ • Website: https://jessewoodbury.com/ HELP GROW SP: • Join Sales Players Slack Community: https://www.launchpass.com/saas_sales_players/free • Su...
Apr 30, 2025•10 min
Jesse talks about mindset shifts sellers can embrace for long-term success. SPONSORS: • Surfe (LinkedIn Prospecting Streamlined) - SP Promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury EPISODE LINKS: • Pre-Order Commission Impossible! - https://www.salesplayers.co/products/ci • Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-coaching-overview CONNECT WITH JESSE: • LinkedIn: https://www.linkedin.com/in/jessewoodbury/ • Website: https://jessewoodbury.com/ HELP...
Apr 24, 2025•17 min
Jesse shares ideas for how you can become a more fierce competitor in your deals. SPONSORS: • Surfe (LinkedIn Prospecting Streamlined) - SP Promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury • Fathom (#1 AI Notetaker) - SP Promo link: https://fathom.partnerlinks.io/salesplayers EPISODE LINKS: • Mutual Action Plan: https://docs.google.com/presentation/d/1br4CrpdOq-3ToypxCTWQ75Ea9DbKtpWSU_bTcKK_TiE/edit#slide=id.p • Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/...
Apr 16, 2025•12 min
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 Sales. SPONSORS: • Surfe (LinkedIn Prospecting Streamlined) - SP Promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury • Fathom (#1 AI Notetaker) - SP Promo link: https://fathom.partnerlinks.io/sale...
Apr 10, 2025•49 min
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 jesse@salesplayers.co to share: #1 What keeps you coming back to the show? #2 What topics would you like to hear more about? For a few of you, I'll pay you for your time giving me feedback on how I can make Sales Players better. Thank you! SPONSORS: • Surfe (LinkedIn Prospecting Streamlined) - SP Promo link: https://www.surfe....
Apr 06, 2025•16 min
Jesse shares the 10k play for developing a PoV when reaching out to executives at public companies. SPONSORS: • Surfe (LinkedIn Prospecting Streamlined) - SP Promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury • Fathom (#1 AI Notetaker) - SP Promo link: https://fathom.partnerlinks.io/salesplayers EPISODE LINKS: • Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-coaching-overview CONNECT WITH JESSE: • LinkedIn: https://www.linkedin.com/in/jessewoodbury/ • Websi...
Apr 04, 2025•10 min
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: • Surfe (LinkedIn Prospecting Streamlined) - SP Promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury • Fathom (#1 AI Notetaker) - SP Promo link: https://fathom.partnerlinks.io/salesplayers EPISODE LINKS: • Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-coaching-overview CONNECT WITH JESSE: • Lin...
Mar 29, 2025•16 min
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: • Surfe (LinkedIn Prospecting Streamlined) - SP Promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury • Fathom (#1 AI Notetaker) - SP Promo link: https://fathom.partnerlinks.io/salesplayers EPISODE LINKS: • Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-coaching-overview CONNECT WITH JESSE: • LinkedIn: http...
Mar 24, 2025•26 min
Jesse shares some ideas for choosing a winning startup by drawing from his own experience working in early startups as a seller. SPONSORS: • Surfe (LinkedIn Prospecting Streamlined) - SP Promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury • Fathom (#1 AI Notetaker) - SP Promo link: https://fathom.partnerlinks.io/salesplayers EPISODE LINKS: • Books Mentioned: Play Bigger, Crossing the Chasm CONNECT WITH JESSE: • LinkedIn: https://www.linkedin.com/in/jessewoodbury/ • Website: https://jessewoo...
Mar 20, 2025•30 min
Jesse shares insights on the current state of tech sales hiring with ideas for how to ace your next interview. SPONSORS: • Surfe (LinkedIn Prospecting Streamlined) - SP Promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury • Fathom (#1 AI Notetaker) - SP Promo link: https://fathom.partnerlinks.io/salesplayers EPISODE LINKS: • Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-coaching-overview CONNECT WITH JESSE: • LinkedIn: https://www.linkedin.com/in/jessewoodbu...
Mar 06, 2025•28 min
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: • Surfe (LinkedIn Prospecting Streamlined) - SP Promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury • Fathom (#1 AI Notetaker) - SP Promo link: https://fathom.partnerlinks.io/salesplayers EPISODE LINKS: • Connect with Amanda: https://www.linkedin.com/in/amandamcrooks/ • BlinkMetrics: https://blinkmetrics.com/ • From Chaos to Cla...
Feb 26, 2025•48 min
Jesse shares some tips for getting the most out of your sales meeting recordings tool (Gong, Chorus etc.) SPONSORS: • Surfe (LinkedIn Prospecting Streamlined) - SP Discount link: https://www.surfe.com/?kfl_ln=jesse-woodbury EPISODE LINKS: • Get Fathom: Get Fathom: https://fathom.partnerlinks.io/salesplayers CONNECT WITH JESSE: • LinkedIn: https://www.linkedin.com/in/jessewoodbury/ • Website: https://jessewoodbury.com/ HELP GROW SP: • Join Sales Players Slack Community: https://www.launchpass.com...
Feb 19, 2025•23 min
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: • Surfe (LinkedIn Prospecting Streamlined) - SP Discount link: https://www.surfe.com/?kfl_ln=jesse-woodbury EPISODE LINKS: • Connect with Chris: https://www.linkedin.com/in/chrisdankowski/ • Website: https://www.dankow.s...
Feb 12, 2025•55 min
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: • Surfe (LinkedIn Prospecting Streamlined) - SP Discount link: https://www.surfe.com/?kfl_ln=jesse-woodbury CONNECT WITH JESSE: • LinkedIn: https://www.linkedin.com/in/jessewoodbury/ • Website: https://jessewoodbury.com/ HELP GROW SP: • Join: https://www.salesplayers.co/ • Subscribe! • Leave a rating, write a revie...
Feb 07, 2025•32 min
*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 the power of internal champions and genuine customer relationships. SPONSORS: • Leadfeeder (Turn Page Views into Pipeline) - https://leadfeeder.partnerlinks.io/rsscjriylqgb - SP fans use ...
Jan 16, 2025•32 min
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 Slack community. SPONSORS: • Leadfeeder (Turn Page Views into Pipeline) - https://leadfeeder.partnerlinks.io/rsscjriylqgb - SP fans use this link for an extended, 21-day free trial • Salesblaz...
Jan 06, 2025•48 min
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 advisor. He joins the Sales Players to share how sellers and leaders can build their subject matter expertise and turn expertise into pipeline. SPONSORS: • Leadfeeder (Turn Page Views into Pipeline) - ...
Dec 19, 2024•44 min
