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/...
Radio and PodcastLive Radio & Podcasts
Business
SaaS Sales Players
Interviews with the SaaS industry's top performing sellers. SaaS Sales Players breaks down the mindset, habits and processes used by software's most successful revenue producers to crush quo...
Episodes
20 of 205 episodesLessons 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/?ut...
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_s...
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...
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:/...
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...
Your Network Is Doing More for Your Sales Career Than You Think
Jesse shares ideas for getting yourself out there and building your network. SPONSORS: ChatAE (AI Account Planning): https://www.chatae.ai/?...
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 t...
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...
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.ch...
What My Former Sales Leader Taught Me About Red Zone Selling with Vince Beese
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...
20 Sales Plays I Run When Nothing Else Is Working
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,...
Building Financial Security as a Tech Seller
Jesse (who is not giving financial or investment advice) shares why tech sellers have a huge advantage when it comes to building wealth and...
The Anonymous Tech Seller Who Built a 6-Figure Side Hustle with "Fidel Cache Flow"
Jesse sits down with " Fidel Cache Flow ," an anonymous tech seller who’s built a cult following on Sales Twitter with unfiltered takes on c...
23 Absolute Truths About Enterprise Selling
Jesse breaks down 23 hard-earned truths about enterprise sales that every seller should know SPONSORS: ChatAE (AI Account Planning): https:/...
What Top Tech Sales Candidates Do Differently
The best candidates don’t just show up, they sell themselves at every step. In this episode, Jesse shares the high-leverage interview plays...
Top Tech Sellers Share These 10 Traits
Jesse breaks down the 10 traits that separate good reps from top-performing enterprise and mid-market sellers. After a decade in tech sales...
What I Learned (the Hard Way) as a Founding AE
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...
This Is Exactly How I Approach Cold Calls Every Day
Jesse breaks down the exact cold call routine he uses daily to drive pipeline. SPONSORS: ChatAE (AI Account Planning): https://www.chatae.ai...
Want Bigger Deals? Learn the Product
Jesse reminds sellers why understanding the product matters, especially when selling to IT buyers. SPONSORS: ChatAE (AI Account Planning): h...