Kalepa, a New York company that sells AI software to insurers, raised $75m in a Series B round at a $470m valuation, it announced on 5 November 2026.
Updata Partners led the round, and existing investors IA Ventures and Inspired Capital took part. Kalepa said it has raised $91m in total.
It is the company's first raise since a $14m Series A in 2021. Over the past year Kalepa's revenue and customer count have each tripled, and it has been cash-flow positive for more than two years, the company said.
“Insurance runs on the judgment of experienced professionals, and our Professional Grade AI is held to that same standard,”Paul Monasterio, Co-founder and CEO, Kalepa
What Kalepa does
Paul Monasterio and Danny Hillman founded Kalepa in New York in 2018, after working with insurers at Applied Predictive Technologies, according to AlleyWatch. They had seen insurers make large decisions with scattered information and a great deal of manual work.
The software started with underwriting and operations, such as assessing submissions and handling quotes, and is moving into pricing and portfolio management. AI agents do the work, coordinated by a layer built for insurance that sets how much autonomy each task gets according to its risk and passes work to people when expertise or approval is needed. Each result is checked so it can be traced and audited.
Customers include W.R. Berkley, Bowhead Specialty and the managing general agent AmRisc. AlleyWatch reported that Kalepa charges according to the book of business it supports and the outcomes it delivers, so its revenue grows as customers use it across more teams and lines of business.
Results the company reports
Kalepa said insurers using its platform report 30% to 60% more premium per underwriter, quotes produced 58% faster, a 960-basis-point improvement in combined ratio and twice the rate of quotes turning into bound policies. The volume of work running through the platform grew fourfold in the past year. The figures come from the company and were not independently verified.
"Insurance runs on the judgment of experienced professionals, and our Professional Grade AI is held to that same standard," said Monasterio, Kalepa's co-founder and chief executive. He said insurers should decide task by task whether a person or AI does the work best and at what cost, leaving staff free for complex risks, close calls and broker relationships.
What the money is for
Kalepa plans to widen its product range, enter new markets and double its headcount in 2027, mostly in engineering, AI and commercial roles. AlleyWatch reported that it plans further expansion in Europe over the next six months. The company did not disclose its current headcount.
It has recently hired Garrett Schlesinger as chief technology officer after 12 years at Affirm, David Meister from Addepar as chief revenue officer, Audrey Howell, formerly of Palantir and Butterfly Network, as head of product, and Tim Khoo-Jones, previously head of talent at Block and Shopify.
Why raise now
Monasterio told AlleyWatch that because Kalepa generates cash, it could choose when to raise, and that the new capital lets it invest more heavily in growth. He said closing the round was relatively easy; the harder part was picking partners who shared the company's views on scale and investment.
Kalepa is focused first on property and casualty insurance, with a longer-term aim of covering the whole insurance value chain, AlleyWatch reported. The $91m total it reports is $2m more than the two rounds it has disclosed; the company did not explain the difference.
Company website: kalepa.com