Kalepa has raised $75 million in a Series B round at a $470 million valuation. Updata Partners led the round, with IA Ventures and Inspired Capital joining, and the new money takes the New York startup to $91 million raised in total.
Kalepa announced the round on November 5, after a year in which it tripled revenue and customer numbers. The volume of work running through its platform grew fourfold over the same period, and the company has been cash flow positive for more than two years.

A year of tripled growth
Kalepa builds AI for commercial insurers. Its platform performs and orchestrates work across operations, underwriting, pricing and portfolio management, and its customers include W.R. Berkley, Bowhead Specialty and AmRisc.
Insurers using Kalepa have reported 30 to 60 per cent more premium per underwriter, a 58 per cent reduction in quote time and double the quote to bind rate. The company also points to a 960 basis point improvement in combined ratio for customers on its platform.
“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 CEO of Kalepa.
Monasterio said the funding lets Kalepa bring its AI to more of the work insurers do, so they can choose between AI and people across the whole value chain.
Where the money goes
Kalepa will use the funding to expand its AI product suite, move into new markets and double its headcount in 2027. Most of the hiring will be in engineering, AI and commercial roles, and the company is also moving into insurance product development, reinsurance and distribution.
The company has added several senior leaders over the past year. Garrett Schlesinger joined as chief technology officer in October after 12 years at Affirm, where he was the company’s 12th employee. David Meister joined as chief revenue officer, Audrey Howell as head of product and Tim Khoo-Jones as head of talent.
A long road from the first round
Kalepa was founded in 2018 by Paul Monasterio and Daniel Hillman, and launched an AI powered copilot for commercial underwriters. Its last round was a $14 million Series A in 2021, led by Inspired Capital with IA Ventures taking part.
The Series B is the company’s first raise in five years. With $91 million raised in total, Kalepa now plans to take its platform to more insurers and more of the work they do.


