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_partn ...
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=salespla ...
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/?utm_source=salesplayers&utm_medium=email&utm_campaign=fall2025_partnership
SPONSORS:
ChatAE (AI Account Planning): https://www.chatae.ai/?utm_source=salesp ...
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 ...
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.sale ...
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 Coachi ...
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 ...
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/1Ko2yq ...
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/1Ko ...
Empowering Sales Professionals: Sarah Brazier Reveals the Key to Effective Solutions
Have you ever heard these common myths about sales? Myth #1: Sales is allabout selling products. Myth #2: Salespeople are born, not made. Myth #3: The key to sales success is having a magnetic personality. In this episode, our guest Sarah Brazier will debunk these myths and share the truth about ...
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