Sales Players

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: https://docs.google.com/document/d/1Ko2yqyLeZ-GdVCDaiROomtZrvvNw50Y3/edit • Schedule 1:1 Coaching Consult: https://calendly.com/jessewoo...

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: https://docs.google.com/document/d/1Ko2yqyLeZ-GdVCDaiROomtZrvvNw50Y3/edit • Schedule 1:1 Coaching Consult: https://calendly.com/jessewoodbu...

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: https://docs.google.com/document/d/1Ko2yqyLeZ-GdVCDaiROomtZrvvNw50Y3/edit • Schedule 1:1 Coaching Consult: https://calendly.com/jessewoodbury/...

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 Consult: https://calendly.com/jessewoodbury/1-1-coaching-overview CONNECT WITH JESSE: • Lin...

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: https://www.salesplayers.co/posts/copy-my-re-engagement-email-template CONNECT WITH JESSE: • LinkedIn: https://www...

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: https://calendly.com/jessewoodbury/paid-coaching-session CONNECT WITH JESSE: • LinkedIn: ht...

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): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership EPISODE LINKS: • Order Red Zone...

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): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership EPISODE LINKS: • Aug '25 Only Coachi...

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): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership EPISODE LINKS: • Connect with Sai: https://www.linkedin.com/in/sguduguntla/ • Get Hyperbou...

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: https://calendly.com/jessewoodbury/1-1-coaching-overview CONNECT WITH JESSE: • LinkedIn: https://www.linkedin.com/in/jessewoodbury/...

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 compet...

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): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership EPISODE LINKS: • h...

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 Planning): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_pa...

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 empl...

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: https://www.salesplayers.co/posts/23-absolute-truths-about-enterprise-selling • Book FREE 1:1 Coaching Intro with Jesse: htt...

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): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership EPISODE LINKS: • Join the FREE Sales Players Slack Community: https:...

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): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership EPI...

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): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership EPISODE LINK...

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 with Jesse: https://calendly.com/jessewoodbury/1-1-coaching-overview CONNECT WITH JESSE: • Link...

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: https://calendly.com/jessewoodbury/1-1-coaching-overview CONNECT WITH JESSE: • LinkedIn: https://...

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 with Jesse: https://calendly.com/jessewoodbury/1-1-coaching-overview CONNECT WITH JESSE: • Lin...

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 FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-coaching-over...

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 Jesse: https://calendly.com/jessewoodbury/1-1-coaching-overview CONNECT WITH JESSE: • LinkedIn: h...

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: https://calendly.com/jessewoodbury/1-1-coaching-overview CONNECT WITH JESSE: • LinkedIn: https://www.linkedin.com/in/j...

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! - https://www.salesplayers.co/products/ci • Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-coac...