Insurance AI Start-Up Kalepa Raises $75 Million at a $470 Million Valuation

Growth equity firm Updata Partners led the round, with existing backers IA Ventures and Inspired Capital also investing. It is the company's first outside raise since 2021, when it took $14 million in a Series A led by Inspired Capital, and it lifts total funding to $91 million.

The deal puts a substantial price on AI built for one narrow, document-heavy profession rather than for general office work. Kalepa's software does not replace the underwriter's judgement so much as handle the gathering, checking and pricing work around it, and the company sells it on auditability as well as speed: it says verification and traceability are built in so insurers can see how a result was reached.

Kalepa was founded in 2018 by Paul Monasterio, its chief executive, and Danny Hillman. Its AI agents run across insurers' operations, underwriting, pricing and portfolio management, passing tasks to human staff where expertise or approval is needed. Customers include the global insurance group W.R. Berkley, specialty insurer Bowhead Specialty and managing general agent AmRisc.

The company said insurers using the platform report 30% to 60% more premium written per underwriter and a 58% cut in the time it takes to produce a quote. In an interview with AlleyWatch it also cited a 960-basis-point improvement in combined ratio, the measure of claims and expenses against premium income, without saying over what period or across which customers. The figures are Kalepa's own and have not been independently verified.

The volume of work running through the platform grew fourfold over the past year, according to the company. AlleyWatch reported that revenue and customer numbers tripled over the same period and that Kalepa has been cash-flow positive for more than two years.

Kalepa does not charge per user. "Insurers pay in proportion to the book of business we support and the outcomes that Kalepa delivers," Monasterio told AlleyWatch, adding: "We intend for Kalepa to become the core platform through which insurers run their businesses."

The company plans to spend the new money on expanding its AI product suite, entering new markets and doubling its headcount in 2027. Monasterio said the newer areas of expansion include insurance product development, reinsurance and distribution. "Most of our hiring will be in engineering, AI, and commercial roles," he said.

Kalepa's initial focus is property and casualty insurance. It has recently hired senior leaders who previously worked at Affirm, Addepar, Palantir, Block and Shopify, and it named Europe to AlleyWatch as the near-term priority for its international expansion.