23 Absolute Truths About Enterprise Selling

SaaS Sales Players by Jesse Woodbury

Jun 9, 202500:04:25Business

Jesse breaks down 23 hard-earned truths about enterprise sales that every seller should know SPONSORS: ChatAE (AI Account Planning): EPISODE LINKS: • Read the 23 Truths: • Book FREE 1:1 Coaching Intro with Jesse: CONNECT...

Related Episodes

Continue listening to more episodes from SaaS Sales Players.

Making the Most of Your Tech Sales Career

Oct 17, 2025 - 00:10:30

Jesse shares lessons on making the most of the tech sales career opportunity. SPONSORS: ChatAE (AI Accoun...

Lessons on Building a Personal Brand from 5 Years of Podcasting

Sep 19, 2025 - 00:15:12

Lessons on (personal) brand building from 5 years of hosting this podcast. SPONSORS: ChatAE (AI Account P...

20 Questions I Use to Stress-Test My Deals

Sep 17, 2025 - 00:13:13

Jesse shares 20 go-to questions for introducing friction in your deals. SPONSORS: ChatAE (AI Account Plan...

What I’m Hearing: Sales Trends Shaping Tech in 2025

Sep 10, 2025 - 00:15:21

Jesse shares insights on trends he's hearing about from conversations with sales leaders, founders, and r...

How I Re-Engage Closed-Lost Opportunities

Aug 28, 2025 - 00:05:24

Jesse shares his approach to building pipeline from the closed-lost deals in your territory. SPONSORS: Ch...

5 Habits That Close More Deals

Aug 19, 2025 - 00:12:02

Jesse shares five simple but powerful habits that increase your chances of closing more deals. SPONSORS:...

Your Network Is Doing More for Your Sales Career Than You Think

Aug 13, 2025 - 00:12:59

Jesse shares ideas for getting yourself out there and building your network. SPONSORS: ChatAE (AI Account...

5 Ideas for Turning Your Sales Skills Into Extra Income

Aug 9, 2025 - 00:22:19

Jesse shares five side hustles that B2B sellers can launch without leaving their day job. He walks throug...