"From Startup Founder to Insurance Innovation Leader: Hard Truths About InsurTech from IMA’s Garrett Droege"

The Leadership in Insurance Podcast - Insurtech & Innovation

In our latest Leadership in Insurance Podcast episode, I sat down with Garrett Droege (SVP, Director of Innovation & Digital Risk Practice Leader at IMA Financial) for a fascinating discussion on InsurTech with some thought-provoking insights that challenge conventional thinking about insurance technology.

With 20 years exclusively on the brokerage side, Garrett brings a unique perspective as a former startup founder and self-taught software developer.

As both Innovation Lead and Digital Risk Practice Leader at IMA, his role sounds incredibly broad, but as Garrett says, both sides serve each other—you need wide ranging touchpoints across tech ecosystems to stay ahead in both innovation and risk.

In this episode, we cover:

Build vs. Buy Decision Framework: Garrett's approach is clear: build customer-facing proprietary solutions that differentiate your business and serve your customers, but make sure it works with existing technology.

The POC Framework That Actually Works: Forget 12-month POCs that drag on and lose momentum. Garrett advocates for highly targeted, 45-60 day maximum POCs with clear KPIs and the right team selection upfront. His advice to founders? "You think you want a 12-month contract. You don't. Let's prove your platform works fast and furiously, or let's wait until you're ready."

The Bold Take: Garrett’s view on how the industry has gone about InsurTech all wrong and allowed it to become a series of Band-Aids for the real problem: antiquated core systems from the 1980s and 90s that were built before APIs even existed. The result? Frankenstein workflows requiring 7-15 platforms to complete a single task, with 80% of users still working around the technology the same way they did 20 years ago.

The AI Wake-Up Call: Despite AI being "transformational unlike anything we've ever seen" (and Garrett argues it's under-hyped), its promise is severely limited without access to core data systems. Garrett stated "You could build a fully agentic AI brokerage much easier than you could reverse engineer and retrofit an existing brokerage."

The Investment Landscape: With 80% of recent Y Combinator and Broker Tech Ventures companies being AI-focused InsurTech solutions, the momentum is undeniable. The dot-com parallels are real—there will be winners and losers, and consolidation is coming.

What Technology Can't Replace: Despite all the transformation, some challenges remain timeless: renewal management, client communication, trust-building. As Garrett notes, these require human expertise that AI augments rather than replaces.

This conversation is essential listening for anyone in insurance, InsurTech, or risk management. The future of insurance isn't just about innovation—it's about getting the foundation right first.

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