Welcome to episode 100! I’m joined by Chuck Ganapathi, Gainsight’s new CEO, for a wide-ranging, candid conversation about where customer success is headed and what leaders should do right now.

We start with Chuck’s career through four platform eras: mainframe to client/server to cloud to AI - and how those shifts shape strategy. He shares the little-known origin story of “Customer Success” at Salesforce, Gainsight’s early days, and why integrations (Salesforce, SAP CX, Microsoft Dynamics) are never “done”—they’re living systems that demand clean data and constant tuning.

Then we dig into Chuck’s concept of Retention-as-a-Service. In a world where retention is existential, the 80/20 mindset breaks. Every dollar matters, which means every customer matters. We talk agentic AI (augmentation vs autonomy), how a “renewal agent” can cover the long tail, and why the magic is orchestration—letting agents handle the repeatable while humans lean into judgment, relationships, and value.

We close with practical automation stories, a few resources Chuck follows, and a reminder that the human-to-human piece isn’t going anywhere.

Links in Today's Episode:

• Ethan Mollik: One Useful Thing
• Saanya Ojha
• Jamin Ball: Clouded Judgement
• Andrej Karpathy on the Dwarkesh Podcast: AGI is still a decade away

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The Digital Customer Success Podcast is hosted by Alex Turkovic

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