// Podcast

Context Window

AI, Insurance & The Humans Behind It

// What to expect

Context Window is Dearborn Labs' podcast for the leaders, operators, and founders working at the intersection of AI and enterprise operations. Each episode is a candid conversation with the people actually putting AI into production inside legacy industries like insurance — what's working, what isn't, and what it really takes to move from pilot to production.

// Latest Episode

Episode 6: Will AI Take Your Job?

CONTEXT WINDOW / EP.06

Will AI Take Your Job?

SEPTEMBER 15, 2026•DURATION: 53 MIN•EPISODE 6

Will AI Take Your Job?

Rick McCathron, President & CEO of Hippo, on AI's impact on jobs, his path through insurance, and turning better technology into operational results.

// Weekly Despatch

New episodes drop regularly. Follow us.

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