Insurtech at Speed: Engineering the Future of Specialty Insurance | The Pair Program Ep88

In today’s episode, we’re joined by Nathan Hall, Chief Technology Officer at Ledgebrook, and Mike Mansell, investor at American Family Ventures, for a deep dive into how modern technology is reshaping specialty insurance. The conversation explores how speed, automation, and broker-first design are redefining underwriting, where AI truly adds value, and why human judgment still matters in high-stakes, regulated industries. From infrastructure decisions to investor signals, this episode unpacks what it really takes to modernize insurance from the inside out.

Here’s what we get into:

1. Why legacy insurance workflows struggle to keep up with modern risk
2. Building for speed without sacrificing trust or compliance
3. How AI augments underwriters instead of replacing them
4. What investors look for in the next wave of insurtech platforms
5. Designing technology around real broker behavior, not ideal workflows

About Nathan Hall: Nathan is the CTO at Ledgebrook, where he leads platform architecture and engineering. With a background spanning SaaS, fintech, and healthcare, he specializes in scaling teams and building systems that prioritize speed, reliability, and real-world usability.

About Mike Mansell: Mike is an investor at American Family Ventures, an early-stage insurtech VC firm. He works closely with founders building the future of insurance, bringing an operator-focused perspective on product-market fit, traction, and long-term defensibility.

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