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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/jessewoo…
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/?…
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_…
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 enterp…
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 Planni…
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