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Rich Lane joins Warren Kucker to discuss Building a Custom GPT for Every Rep on Your Team. Key takeaways include Sales coaching with AI and Differentiating coaching, training, and feedback.

EP. 4 27 min January 20, 2026 Recorded January 20, 2026

Building a Custom GPT for Every Rep on Your Team

with Rich Lane

"AI Will Expose the Managers Who Were Never Actually Coaching"

About This Episode

This episode explores innovative AI applications in sales coaching, examining both opportunities and challenges. The discussion covers how custom GPT tools can enhance coaching effectiveness, the distinction between coaching, training, and feedback, and critical implementation considerations for sales leaders.

About the Guest

Rich Lane

Head of Commercial at Kepler, specializing in leveraging AI to enhance sales coaching practices and rep development.

Key Takeaways

  • Sales coaching with AI
  • Differentiating coaching, training, and feedback

Chapters

00:00 Transition into Sales and Coaching
06:36 Custom GPT for Sales Coaching
15:05 Impact of AI on Sales Coaching
23:41 Mistakes to Avoid in Implementing AI in Sales Coaching
Account ExecutivesSales ManagersRevenue OperationsVPs of SalesCRO

About the Host

Selling AI is hosted by Warren Kucker, founder of Topiq. Each week he sits down with revenue leaders, founders, and operators to unpack the strategies, tools, and stories behind selling AI products and using AI to sell smarter.

Warren Kucker — Host of Selling AI

Warren Kucker

A revenue leader and entrepreneur who founded Basiq.work, focusing on conversational AI for sales teams. Previously served as VP of Sales and CRO at Series B companies, scaling revenue to $2M+ quarterly bookings. His exits include Shelly.ai (ML email automation) and Boxton (digital freight platform). Started his career at Apple managing a $100M shipping efficiency program.