Kalepa Raises $75 Million Series B at a $470 Million Valuation. What the Long Gap From Series A Signals for New York Founders
New York insurtech Kalepa announced a $75 million Series B at a $470 million valuation after staying cash flow positive for more than two years. Here’s what the raise, the product, and the hiring spree mean for founders building in regulated industries.
NEW YORK — Five years after its Series A, New York insurtech Kalepa came back to market with a much larger check — and a story that runs against the usual AI fundraising script.
On Nov. 5, 2026, the company announced a $75 million Series B at a $470 million valuation, led by Updata Partners with participation from IA Ventures and Inspired Capital. Kalepa has now raised $91 million in total. Its last round was a $14 million Series A in 2021 led by Inspired Capital with IA Ventures.
A Raise Built on Patience, Not Hype
What stands out for New York founders is not only the size of the round. Kalepa says it has been cash flow positive for more than two years, tripled revenue and customer count over the past year, and chose when to raise rather than racing back to the market after the Series A. In an AlleyWatch interview, co-founder and CEO Paul Monasterio said the company had “the advantage of choosing when to raise” because it had built a growing, cash-generating business.
That long Series A-to-B gap is a useful signal. In regulated verticals, product-market fit often means insurers putting the software into production, expanding seats, and keeping it through audit season — not a viral demo. Kalepa’s own framing is that it invested in customer results and disciplined capital use first, then raised to accelerate.
Kalepa was founded in New York in 2018 by Monasterio and Daniel Hillman, according to AlleyWatch. Monasterio is co-founder and CEO. The company’s customers named in the announcement include W.R. Berkley, Bowhead Specialty, and AmRisc.
What “Professional Grade AI” Means in Insurance
Kalepa describes its product as Professional Grade AI agents for insurance across operations, underwriting, pricing, and portfolio management. The pitch is not a chatbot bolted onto a submission inbox. The company says its platform coordinates agents behind connected workflows, matches autonomy to each task and its risk, brings people in where expertise or approval is needed, and verifies every result so it can be traced and audited — a requirement in a regulated industry where decisions can carry consequences for years.
That audit trail point matters for any New York founder selling AI into banks, insurers, health systems, or government contractors. Buyers in those markets ask who did the work, why the model recommended it, and whether the result can survive an exam. Kalepa is selling into that exact constraint.
Company-reported metrics from insurers using Kalepa include 30% to 60% more premium per underwriter, a 58% reduction in quote time, a 960-basis-point improvement in combined ratio, double the quote-to-bind rate, and a 4x increase in the volume of work running through the platform over the past year. Those figures come from Kalepa’s announcement; they are not independent third-party audits.
Hiring Into New York’s Insurance and Fintech Talent Market
Kalepa says it will use the new capital to expand its AI product suite, move into new markets, and double headcount in 2027. Recent senior hires named in the release include Garrett Schlesinger as chief technology officer (formerly of Affirm), David Meister as chief revenue officer (formerly of Addepar), Audrey Howell as head of product (formerly of Palantir and Butterfly Network), and Tim Khoo-Jones as head of talent (formerly of Block and Shopify).
For New York’s insurance and fintech talent market, that roster is a tell. The city still concentrates underwriting, specialty insurance, MGAs, and capital-markets tech. When a local insurtech raises at this scale and staffs up from Affirm, Addepar, and Palantir alumni, it pulls from the same hiring pools as banks, brokers, and Series A fintechs. Agencies and consultants that sell into insurers should also watch the customer list: Berkley, Bowhead, and AmRisc are the kinds of accounts that often expand vendor stacks after a successful underwriting pilot.
Takeaways for New York Founders
- Cash flow can be a fundraising strategy. A long gap between rounds is not automatically a red flag if revenue, retention, and unit economics are real.
- Regulated buyers buy auditability. If your AI cannot show what happened and why, expect a longer sales cycle in insurance and adjacent markets.
- Vertical agents are still the New York bet. Kalepa fits the same pattern as other industry-specific AI companies raising here: deep workflow ownership beats generic copilots.
- Headcount plans move local talent. A planned doubling in 2027 means more competition for AI, engineering, and go-to-market people who already understand financial services.
Kalepa’s Series B will not settle every debate about AI in underwriting. It does, however, show what a New York company can look like when it waits for production proof before taking a growth check — and what insurers say they need when the agents touch real risk decisions.