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

Today on our show it’s no news, just thank yous.

It’s been a roller coaster of a year for everyone, and despite everything, you have tuned in. Walking your dog, on the way to work, even in the shower you were there. Listening, laughing, cringing, and hopefully, even learning.

I started this podcast back in 2021 and look forward to doing it for many more years. The fact that our content and presence continue to grow each year is a testament to you.

So, here it is. Thank you for listening. If you like what we’re doing, reach out. Tell us what you like about it, recommend it to a friend. And of course, have a Happy Holidays wherever the end of this year takes you.

This is Rick Watson, signing off for the year. I also wanted to say a huge thank you to my partners in crime Hendrik, Libby, Kaylea, Jacque, Vinny and Ron, without you this podcast would not be possible.

Today's episode is sponsored by Mirakl.

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

Today on our show:

• Shopify Winter Editions 2025 Special Podcast

- 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 Mirakl.

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

Today on our show:

• Black Friday Cyber Monday - You Devil You!
• Sam Altman Calls a Code Red to Stop Google Threat
• Amazon and Visa Partner on Agentic Payments
• Nike CEO Purges John Donahoe’s Lieutenants

- and finally, The Investor Minute which contains 3 items this week from the world of venture capital, acquisitions, and IPOs.

Today's episode is sponsored by Mirakl.

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

Today on our show:

• Walmart Plans a CEO Transition
• Commerce Operations Foundation Critical to Our Common Agentic Future
• Intuit's Announcement Makes it Clear: OpenAI Coming for Operating Systems
• Walmart Earnings Call Important for Everyone to Understand

- 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

Today on our show:

• Same-Day Facilities Key to Amazon's New Powerful Grocery Strategy
• Walmart CEO Doug McMillion Steps Down
• TheRealReal Records Record GMV During Earnings
• Google Releases Some AI Shopping Updates

- 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