Kalepa, the New York company that sells AI software to insurance underwriters, said on 5 November 2026 that it had raised a $75 million Kalepa Series B at a $470 million valuation, led by Updata Partners. Fintechbits checked Kalepa’s own Greenhouse careers board, where the company is advertising for a Director of Talent Acquisition at a posted base salary of $170,000 to $250,000, the hire who would have to deliver its plan to double headcount in 2027. Kalepa says in its announcement that revenue and its customer count both tripled in the 12 months before the announcement.

What Kalepa sells and who buys it

Kalepa, founded in 2018, builds software that runs underwriting work for insurers and managing general agents: taking in submissions, triaging risks, pricing, and managing portfolios. Kalepa calls it “Professional Grade AI”. In practice the platform coordinates AI agents across those steps, decides how much autonomy each task gets, and routes work to human underwriters where a judgment or approval is needed.

The named customers are serious ones. Kalepa lists W.R. Berkley, Bowhead Specialty and AmRisc in the release, and its newsroom shows Church Mutual selected Kalepa for its CM Vantage unit in September. Kalepa says the volume of work running through the platform grew fourfold over the same 12 months.

The performance claims are large and come from customers via Kalepa. The company says insurers using it have reported 30% to 60% more premium per underwriter, a 58% cut in quote time, a 960-basis-point improvement in combined ratio and double the quote-to-bind rate. Kalepa does not say how many customers those figures cover or over what period, and a 960-basis-point combined ratio swing is the kind of number that usually reflects a book being repriced as much as a tool being used.

The Kalepa Series B in context

The Kalepa Series B is the first priced round Kalepa has announced since a $14 million Series A in 2021, led by Inspired Capital with IA Ventures. Both of those investors came back for the Kalepa Series B. Kalepa has raised $91 million in total.

That long gap is the most interesting fact in the release. Kalepa says it has been cash flow positive for more than two years, which means it did not need outside money to keep running. Raising the Kalepa Series B looks like a choice to speed up, not a rescue. Paul Monasterio, Kalepa’s co-founder and chief executive, said the funding “lets us bring Professional Grade AI to more of the work insurers do”.

Kalepa has also hired senior people from bigger fintech names. Garrett Schlesinger joined as chief technology officer in October after 12 years at Affirm, where he was the 12th employee and helped build its real-time underwriting system. Chief revenue officer David Meister came from Addepar.

Fintechbits analysis

Why the Hiring Plan Matters More Than the Valuation

The $470 million valuation in the Kalepa Series B is not outlandish for a profitable vertical software company with tripling revenue. Investors are backing AI underwriting from several angles: Fintechbits covered Great Hill Partners’ stake in Aurenity, an AI-underwriting MGA, in September. The difference is that Kalepa sells to carriers rather than competing with them, which is a cleaner business when underwriting cycles turn.

The harder part is execution. Kalepa says it will use the money from the Kalepa Series B to expand its products, enter new markets and double its team in 2027. Doubling headcount at a company that has been run for cash flow is a cultural change as much as a budget line, and it usually starts with recruiting leadership. The Greenhouse posting is a sign the plan is real, but it also shows the recruiting function is being built from the top, which takes time. The same posting still describes Kalepa as backed by IA Ventures and Inspired Capital, with no mention of Updata.

The other risk is the claims. If Kalepa wants carriers to rethink how work is split between people and software, it will need independent evidence. Agent-to-agent quoting is already live elsewhere in the market, as Fintechbits reported for Thimble and Bold Penguin, so the bar for proof is rising.

Frequently asked questions

How much did Kalepa raise in its Series B?

Kalepa raised $75 million at a $470 million valuation, announced on 5 November 2026. Updata Partners led the Kalepa Series B, with IA Ventures and Inspired Capital participating.

What does Kalepa do?

Kalepa sells AI software that carries out and coordinates underwriting, pricing, operations and portfolio work for insurers and managing general agents. Human underwriters step in where approval or judgment is needed.

Is Kalepa profitable?

Kalepa says it had been cash flow positive for more than two years before the Kalepa Series B. It has not published revenue figures, only that revenue tripled in the 12 months before 5 November 2026.

What to Watch Next

The concrete test of the Kalepa Series B is headcount. Kalepa has committed to doubling its team in 2027, so its careers board should fill with engineering, implementation and sales roles through 2027. A second test is whether Kalepa names new carrier customers outside the specialty and excess lines it lists, since the platform will need broader proof than a handful of logos.