Three Things We Learned — Thanksgiving Week 2025 Edition

Posted on by Nick Coenen

Hi Friends!

We have arrived at Thanksgiving week. I hope you’re able to find a moment to pause, enjoy time with loved ones, and recharge. It’s been a long year filled with change, opportunity, and plenty of spirited conversations across the insurance ecosystem. I’m especially thankful for all of you who read along each week. This community means a lot to me, and I appreciate you being part of it. I’m excited to see where the final stretch of 2025 takes us.

This week, we’re following a mix of AI-driven investment momentum, global expansion moves across capital and capacity, and a fresh round of product and M&A activity shaping year-end strategies.

Here are the Three Things We Learned:

 [1]

AI Investment Momentum Continues to Set the Pace

Federato grabbed headlines with a $100M Series D, underscoring AI’s continued dominance in the insurtech investment landscape. Their underwriting and portfolio intelligence platform has been gaining traction, and this round signals that investors still see meaningful upside in AI tools driving better risk selection and capital efficiency.

We also saw smaller but notable moves that point in the same direction. Pibit.AI raised $7M to keep advancing its AI-powered quoting and servicing tools. At the same time, Liberate and HawkSoft teamed up to bring “agentic AI” into agency workflows, an example of how AI is becoming embedded directly into day-to-day operations across distribution.

On the core systems side, Majesco announced its plan to acquire Vitech, adding more scale and depth to the policy, billing, and admin space at a time when modernization cycles are heating up. And SoftBank trimming its stake in Lemonade below 5% offered a reality check—a reminder of how investor enthusiasm for the early public insurtechs has shifted as growth, scale, and profitability have taken center stage.

 [2]

Global Expansion and New Capital Vehicles Keep Building

Several moves this week focused on unlocking access to global capacity and standing up new capital vehicles. SageSure secured Lloyd’s Coverholder and DCA status to write through Trium Syndicate 1322, a meaningful step that broadens their reach and adds flexibility as they continue scaling.

Obsidian boosted its surplus to support rising demand across its hybrid fronting platform — a move that reflects the maturation of capital-supported growth models in E&S. And Bobcat Re entered the market as a U.S.-based property treaty MGA distributing through London brokers, part of a growing wave of U.S. players leveraging London’s access to specialty appetite.

On the life and reinsurance side, Prudential-backed Prismic Life raised $1.3B to expand its platform. It’s another sign that alternative capital structures and new reinsurance vehicles are rolling forward — giving the market more optionality on where capacity comes from and how it’s deployed.

 [3]

Product Expansion and M&A Close Out a Busy Stretch

Rounding out the week, we saw several moves centered on product expansion and strategic combinations. Coterie Insurance and Progressive announced a new collaboration to broaden access to BOP and GL products for small businesses — blending digital underwriting efficiency with carrier distribution strength.

Progressive also posted strong October results, reporting an 89.7% combined ratio, 11% written premium growth, and $846M in net income. It’s a solid performance that adds more weight to their partnership with Coterie and reinforces the competitive nature of the SMB market.

MS&AD advanced its investment strategy by agreeing to acquire a stake in Barings from MassMutual, building longer-term asset-management capabilities. And Amynta expanded its nonprofit portfolio with the acquisition of NPS, adding scale at a time when specialty-focused M&A shows no signs of slowing.