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The Insurtech Leadership Podcast

The conversations shaping insurtech.

Joshua Hollander speaks with the operators, founders, and investors shaping insurtech. New episodes weekly.

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Every episode is one leader in insurance or insurtech on what they are building, who they are hiring, and where the market is going.

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October 26, 2026 · 39 min

The Conference Pivot: Insurtech Events in 2027 with Stacey Brown

What happens to a startup pitch when every single submission in the pile says AI on it? Stacey Brown has a useful vantage point on that question, because his Innovation Challenge is one of the few places where carriers actually sit down and read what startups send them. Submissions for the 2026 challenge close on October 7, roughly sixty had come in when this conversation was recorded, and Stacey…

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