WARNING: If you lead a sales org and you're missing quota… this episode will hit uncomfortably close to home. BUT, help enormously with your plans to bridge the GAP too.
To celebrate our 100th episode of WMYT, we brought in Keenan, author of Gap Selling, for a raw, unfiltered teardown of what’s really broken in most B2B sales teams today.
The harsh reality: most sales orgs, even at top-tier tech companies, are built on broken foundations.
And until CROs and founders fix the underlying system, no enablement playbook, tech stack, or recruiter will save them.
What You’ll Learn:
Why your reps aren’t the problem, your system is
How enablement, ops, and leadership are misaligned (and what to fix first)
Why bloated pipelines and dead opps = weak GTM infrastructure
What most CROs get completely wrong about coaching, hiring, and performance
Why “top talent” fails in broken systems
The KPIs that actually matter: win rate, deal velocity, average contract value
A sneak peek at GAP Prospecting, Keenan’s newest framework for top-of-funnel dominance
Who This Is For:
CROs at Series A to $100M+ tech companies
Founders building out their first real GTM engine
VPs of Sales & RevOps tired of reactive, messy execution
Investors & Advisors who want better performance from portfolio sales teams
Quote Worth Sharing:
"If you haven’t defined the system, the skills, and the standards, don’t expect results." - Keenan
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About Keenan
Keenan is the founder & CEO of A Sales Guy Inc. and the author of the best-selling book Gap Selling , one of the most influential sales books of the last decade. With 25+ years in sales leadership, he’s helped startups to Fortune 500s fix broken revenue teams, implement problem-centric selling, and scale pipeline with precision.
🔗 Connect with Keenan → https://www.linkedin.com/in/jimkeenan/
📘 Check out his work https://salesgrowth.com/
🎙️ About the Host – Richard Washington
Richard Washington is co-host of What Makes You Tick, a GTM recruiter, and a trusted advisor to B2B SaaS companies scaling from $5M to $50M ARR. He helps founders build revenue teams that actually perform, with strategy, talent, and execution that scales.
🔗 Follow Richard on LinkedIn → https://www.linkedin.com/in/richwash/
📩 Read his newsletter Growth Magnet → https://www.linkedin.com/build-relation/newsletter-follow?entityUrn=7083793079794556928
Listen to Tolu's TEDx talk on Oceans https://youtu.be/dp0szAVURwo?si=pYuSJxBTIsBadOjk
Ready to Build a Sales Org That Scales?
👉 Subscribe for tactical GTM strategy, sales leadership, and execution frameworks
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#WhatMakesYouTick #TickTalent #Keenan