CX Decoded Podcast
June 3, 2026
SEASON 5, EPISODE 6
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.
Catching up on College Baseball, Digital Experience
Digital Experience in Insurance: Scaling Care Without Losing the Human Touch
Ben Larsen has a simple way of describing his job as digital experience officer at Wellfleet Insurance: everything above the waterline is what customers see, and everything below it determines what's actually possible. The challenge — and the opportunity — is modernizing both at the same time. In this episode, Larsen joins host Dom Nicastro to talk through what customer experience transformation really looks like inside a 35-year-old student health insurance business, where the competitive advantage has always been a human being on the other end of the phone — and where the pressure to scale that care through digital means has never been greater.
From Contact Center Modernization to Agentic AI
Larsen walks through the small and large bets Wellfleet is placing on conversational AI and agentic customer experience — from customer service chatbots designed to handle low-hanging fruit inside the member app, to longer-term agentic workflows that could reshape how consumers move through the entire Wellfleet experience. He's clear-eyed about the prerequisite: none of it works without clean, structured, accessible data. It's a conversation that will resonate with any digital leader navigating legacy infrastructure, contact center modernization and the very real gap between what AI promises and what your data stack can actually deliver.
Want the video version of this interview? Check out the CMSWire TV's The Digital Experience.