From the Bullpen to the Bot Strategy: Wellfleet's Ben Larsen on Digital Experience in Insurance
Ben Larsen has spent nine years inside a company that built its reputation on something increasingly rare in insurance: actually caring. Wellfleet Insurance — a Berkshire Hathaway company — has answered the phone for college students navigating health insurance for the first time for over three decades, and that white-glove service culture is baked into everything. Now, as Digital Experience Officer, Larsen is the one tasked with figuring out how to take that same care and push it through a screen. In this conversation, Larsen walks Dom Nicastro through the real shape of digital transformation inside a multi-line insurance business — the legacy infrastructure hiding below the surface, the student health advisory council that tells him exactly what Gen Z actually wants, the small and large bets he's placing on bot technology and agentic AI, and why none of it works without getting the data right first. Oh, and there's a Salem State College baseball reunion in here too. You've been warned.
