Most AI pilots fail—at least, that’s the headline. But today’s guest is proving that doesn’t have to be true.

In this Watson Weekly interview, Rick Watson goes behind the scenes with Chris Kellner, CEO of DigitalGenius, to discuss how a decade-old AI pioneer is navigating the modern LLM explosion. We move past the hype to explore how AI is actually rewriting the playbooks for sales, marketing, and customer support.

In this episode, you’ll learn:

* The "Locomotive" Metaphor: Why DigitalGenius didn't have to reinvent itself, but rather accelerated on existing tracks.

* Sales & Marketing Rewired: How Chris’s team uses AI for call coaching, MEDPIC scorecards, and CRM automation to let humans focus on high-value closing.

* UK vs. US Market Mismatch: Why traditional outbound playbooks failed when crossing the Atlantic and what they did to fix it.

*The Competition for Culture: How an internal "Agent-Building" competition spurred unexpected creativity across the company.

3 Hard Lessons in AI Support: The essential checklist for any leader deploying AI in customer service today.

Chapters

00:00 – Intro: Turning AI buzz into customer wins

03:15 – Chris Kellner’s journey from Banking to SaaS CEO

07:40 – Acceleration vs. Reinvention: Building the AI train line

14:20 – Rewiring GTM: AI call coaching and MEDPIC scorecards

22:10 – Market Mismatches: Lessons from scaling from the UK to the US

30:45 – Culture & Internal Adoption: The AI Agent competition

38:30 – Why most AI pilots fail (and how to make yours succeed)

45:15 – Build vs. Buy: When to go in-house and when to use a vendor

52:00 – Closing thoughts and key takeaways

#watsonweekly #ai #customersupport

Today on our show:

1. Walmart Shakes Up Its Leadership Ranks
2. NRF 2026 Recap
3. More Content Coming To You from the Watson Weekly

- and finally, The Investor Minute which contains 4 items this week from the world of venture capital, acquisitions, and IPOs.

Today's episode is sponsored by Rithum.

https://www.rmwcommerce.com/ecommerce-podcast-watsonweekly

Today on our show:

1. It’s Time to Be Bold in 2026
2. Welcome to NRF

- and finally, The Investor Minute which contains 5 items this week from the world of venture capital, acquisitions, and IPOs.

Today's episode is sponsored by Rithum.

https://www.rmwcommerce.com/ecommerce-podcast-watsonweekly