Kalepa raises $75m Series B for AI in insurance underwriting

Kalepa raises $75m Series B for AI in insurance underwriting

5 November 2026: Kalepa says it has raised $75 million in a Series B at a $470 million valuation, led by Updata Partners with IA Ventures and Inspired Capital taking part. The New York company, whose software helps insurers underwrite and price risk, plans to double its headcount in 2027.

Not yet independently verified. The round, the valuation and every performance figure here come from Kalepa's own release. We have not seen an investor post or any independent check of the insurers' results. We will update this when it can be confirmed, and remove this note.

Five years between rounds

Kalepa's previous round was a $14 million Series A in 2021, led by Inspired Capital with IA Ventures, so this one is more than five times larger and takes the total raised to $91 million. The long gap has a stated explanation: the company says it has been cash flow positive for more than two years, and that revenue and customer numbers tripled over the past year while volume through its platform rose fourfold.

The money is for expanding its AI product suite, moving into new markets and that hiring. Recent leadership hires include Garrett Schlesinger as chief technology officer, who joined in October after working at Affirm, David Meister as chief revenue officer, from Addepar, and Audrey Howell as head of product, previously at Palantir and Butterfly Network.

"Insurance runs on the judgment of experienced professionals, and our Professional Grade AI is held to that same standard," said Paul Monasterio, co-founder and chief executive.

What insurers are said to get from it

Kalepa names W.R. Berkley, Bowhead Specialty and AmRisc as customers. The release reports results from insurers using the product: 30% to 60% more premium per underwriter, a 58% reduction in quote time, a 960 basis point improvement in combined ratio and double the quote-to-bind rate.

Those are large claims, and the combined ratio figure in particular deserves a question from any insurer evaluating the product. A combined ratio depends on pricing, claims, mix of business and reinsurance as well as on the underwriting workbench. A prospective buyer can ask which customers and which lines the figure covers, and over how many years.

A category where insurers already have vendors

Underwriting AI sits alongside rating and policy software rather than replacing it, so a carrier or managing general agent will want to know how it connects to the core systems already in place.

We list 14 property and casualty insurance software products and six insurance rating products, and hyperexponential, an insurance pricing software company, is among the listings a buyer might compare. Updata Partners, the lead investor, also has a profile in our catalogue.

The release gives no founding year and no target geography for the new markets it mentions.

Company profile on TrustList: Kalepa

Related on TrustList:

• Casap raises $56M Series B for AI agents that handle card disputes
• RapidCanvas raises $29m to put field AI engineers in mid-size firms
• Simplismart raises $14m Series B led by Dallas Venture Capital

Sources

• Kalepa newsroom: Kalepa raises $75 million Series B, 5 November 2026, 5 November 2026