A New York insurer software company just collected an outsized reward for patience. Kalepa closed a $75M Series B at a $470M valuation, led by Updata Partners, five years after its last raise.
Paul Monasterio and Daniel Hillman co-founded the company. Its customers span MGAs, reinsurers, program administrators and carriers, who lean on it for pricing, portfolio decisions and underwriting. More than 10 countries host those operations.
Real money, not just pilots
Insurers on the platform write over 58% more premium per underwriter and deliver quotes 30-60% faster, Kalepa reports. Its combined ratio improves by 960 basis points, a gauge of how much premium gets eaten by claims and expenses.
The pitch is that agents handle multi-step research while people keep the call. Autonomy scales with task risk, every action stays auditable, and underwriters come in when judgement or sign-off is needed.
An unusual bet for the AI cycle
Waiting five years between rounds is rare while capital chases anything with a model attached. More than two years of positive cash flow let the company wait rather than take the first term sheet offered.
The round lands as AI-native entrants win an outsized share of insurtech dollars and carriers decide whether to build underwriting agents or rent them. Kalepa argues the moat sits in the workflow, not the model.
Its cap table reads like a network. Four names the company lists are Carta chief executive Henry Ward, former US Commerce Secretary Penny Pritzker, Lead Bank chief executive Jacqueline Reses and investor Gokul Rajaram.
Monasterio, holder of an MIT PhD in nuclear science and engineering, says his outsider view helps. Kalepa’s demos skip slides and instead ask prospects to hand over a live risk from their desk.
