# Collin Mitchell

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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: https://calendly.com/jessewoodbury/1-…

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): https://www.chatae.ai/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partners…

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): https://www.chatae.ai/?utm_source=salesplayer…

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: h…

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: https://www.salespl…

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 …

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: https://docs.google.com/document/d/1Ko2yqyLeZ-Gd…

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: https://docs.google.com/document/d/1Ko2yqyLe…

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: https://docs.google.com/document/d/1Ko2yq…

307: Top 25 Lessons of The 20% Podcast (Best of Series)

In this week’s episode, I am celebrating by sharing my favorite lessons from the Top 25 Most-listened episodes of The 20% Podcast which originally aired as Episode 217 of the show. Over the past few weeks, I have shared the Top 20 episodes (links to those episodes below), but wanted to compile all …