Venture Capital

Insurance & InsurTech Investment Intelligence Report: May 4–9, 2026

Insurance & InsurTech Investment Intelligence Report: May 4–9, 2026

$820M disclosed | 4 transactions | Heaviest week of 2026 by capital deployed

Every deal this week is AI-native. Every deal attacks a different layer of the insurance infrastructure stack: claims administration, carrier underwriting, software modernization, and catastrophe capital. Gallagher Re's Q1 2026 report, released simultaneously, confirms the macro: global insurtech funding reached $1.63B in Q1, with AI-focused firms capturing 95% of all capital deployed. This week alone represents half of that quarterly total in five days. The insurance industry is not experimenting with AI. It is funding the companies that will make the current operating model obsolete.

Insurance & InsurTech Investment Report: Week of April 27 – May 2, 2026

Insurance & InsurTech Investment Report: Week of April 27 – May 2, 2026

This wasn’t a big week. It was a decisive one.

Across six transactions, the signal is clear: insurance is consolidating around control—of data, distribution, capital, and underwriting.

From Counterpart taking risk onto its own balance sheet, to Northwestern Mutual turning venture into a distribution strategy, to Baldwin completing a fully integrated insurance stack—this is no longer about incremental innovation.

It’s about who owns the system

Ali Safavi talks about Innovation at a Global scale

Ali Safavi is the Founder and Global Head of Plug and Play Insurtech, an Insurtech-focused innovation platform in partnership with some of the largest insurers, reinsurers and brokers in the world including: Munich Re, USAA, State Farm, SOMPO Digital Lab, Farmers, Nationwide, Deloitte, Willis Towers Watson, Aviva, Swiss Re, and many more. Since its inception, Ali has been a catalyst in building Plug and Play Insurtech to 6 global locations, over 70 corporate partners, 120 accelerated startups, and over 25 insurtech investments. Ali is also a Principal at Plug and Play Ventures, the venture arm of Plug and Play Tech Center where he manages and leads investments in startups in different spaces including insurance, travel and hospitality, and IoT.

We had a lovely InsurTech Talk over wine.

Interview with Dominic DiMarco - Entrepreneur in Residence (EiR) QBE

Insurance companies take active steps towards modernization to keep up with customer's expectations and recent entrants to the insurance space who use the latest technology. Carriers introduced new entities into their organizations to champion and facilitate progress. Today there are innovation teams, innovation labs, venture arms, accelerator programs, and the less familiar function -- the Entrepreneur in Residence (EiR).

To understand better the avant-garde insurance that is done by the large insurance companies and their innovation programs I reached out to the leading insurance innovation teams.

Here is a short interview with Dominic DiMarco, EiR in QBE insurance, the man that claims to have the best job in the insurance industry.

"All the big businesses are trying to figure out how to do things "faster, quicker, easier and leaner" and they don't have those skills in their four walls to do it themselves most of the times."

"There is a difference between the IT infrastructure and core systems to the innovative work that is happening on the fringes. You can't replace a core system at once."

"Insurance companies, at their core, are massive financial institutes."