Top insurtech funding rounds, May 2026

There were about 50 funding events in the insurtech sector in May 2026, according to a review by Digital Insurance. What follows is a selection of these. (Other funding events, such as private-equity infusions, are included in the overall count.)

A portion of the data was sourced from Crunchbase. Other information, including quotes from investing VCs, comes from company announcements. For our previous edition, which covered April, click here. These updates will continue monthly.

Corgi

- Funding: $160 million Series B
- Type of company: Full-stack insurance for startups
- Investors: TCV, with participation from both existing and new investors including Oliver Jung, Leblon Capital, Kindred Ventures, Repeat VC, Zone 2 Ventures, Audeo Ventures, Quadri Ventures, First Order Fund, Vocal Ventures, Maiora Ventures, Nordstar, Seven Stars Ventures, Hexa Capital, Alpha Square Group, GSBackers, OurCrowd, Alumni Ventures, Global Growth Fund, and other strategic investors.

"Insurance is one of the largest industries in the world, but it's still built on infrastructure from centuries ago," said Emily Yuan, co-founder and COO of Corgi, in a press release. "We started with property management and are expanding into trucking insurance, payroll, and small business, automating some of the hardest workflows in the real economy."

Reserv

- Funding: $125 million Series C
- Type of company: Third-party administrator and claims intelligence
- Investors: KKR, with participation from existing investors Bain Capital Ventures and Flourish Ventures.

"We're excited to partner with this high-calibre management team, which has the rare combination of innovation, agility, and operational sophistication to rapidly scale to meet customer needs and deliver differentiated outcomes compared to legacy claims handling approaches," said Elliot Bell, principal at KKR, in a press release. 

Pace

- Funding: $46 million Series B
- Type of company: AI operations software
- Investors: Thrive Capital and Sequoia Capital, with participation from Emergence Capital and Pruven Capital.

"At Thrive, there are two things that really matter to us when investing in a company: ideas whose time has come and people who are really well matched to the problems they're working on," said Philip Clark, partner at Thrive Capital, in a press release. "We are in this really special moment where the most important high value parts of the knowledge economy are being augmented and automated to a significant degree by these models and Jamie is one of those people where you go in biased to saying yes."

Tomorrow.io

- Funding: $35 million Series F
- Type of company: Weather intelligence
- Investors: Pitango and Harel Insurance.

"Our continued investment in Tomorrow.io reflects what we believe defines truly category-shaping companies: visionary founders, a long-term mission, and a partnership that compounds over time. This team isn't simply building a product: they're laying down critical infrastructure for how the world adapts to volatility. We're proud to keep building alongside them," said Aaron Mankovski, managing partner at Pitango, in a press release.

This roundup was created with AI assistance. A Digital Insurance editor reviewed each item before publication.