Sales Players

Updated: 31 Jul 2025 • 197 episodes
www.salesplayers.co

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.

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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. EPISODE LINKS: • Connect with Sai: https://www.linkedin.com/in/sguduguntla/ • Get Hyperbound: https://www.hyperbound.ai/ CONNECT WITH JESSE: • LinkedIn: htt

39 min
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Jesse breaks down the exact numbers he tracks to stay on target and outperform quota. EPISODE LINKS: • 1:1 Coaching Intro: 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

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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 li

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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

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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

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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 d

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