Brent Krempges, Chief Customer Officer at Gainsight, joins the show to unpack the next evolution of Customer Success in an AI-first world.

After 12+ years at Gainsight, from implementation to global pre-sales to CCO,  Brent shares how CS is shifting from seat-based software to outcome-driven operating models. We dive into AI-driven health scores, renewal agents, sentiment analysis, and the looming “retention reckoning” facing AI-native companies.

 Key Takeaways (Bullet Summary)

• AI will elevate — not eliminate — the importance of services.
• Floor-Deployed Engineers (FDEs) signal a return to high-touch value realization.
• Health scores are getting smarter, but “watermelon accounts” will always exist.
• Sentiment analysis from transcripts and email may replace traditional NPS.
• Many AI companies haven’t hit their renewal reality yet.
• Retention pressure is coming — especially for growth-at-all-costs AI startups.
• Before deploying agents, companies must rebuild foundational lifecycle processes.
• Think of agents as “50 interns” — would they know what to do?