Kalepa Raises $75 Million Series B at a $470 Million Valuation to Expand Professional Grade AI Across Insurance

NEW YORK, November 5, 2026 — Kalepa, the leader in Professional Grade AI for insurance, today announced $75 million in Series B funding at a $470 million valuation. Over the past year, the company has tripled revenue and its customer count. Kalepa has sustained this growth while remaining cash flow positive for more than two years, and will use the new funding to expand its AI product suite, move into new markets, and double the team’s headcount in 2027. Its customers include major insurers and MGAs such as W.R. Berkley, Bowhead Specialty, and AmRisc.

Insurers are under pressure from every direction. Losses keep climbing, a generation of experienced professionals is retiring and taking decades of judgment with it, and AI-native competitors are entering the market built for speed from day one. Softening prices leave less room for error on every decision. Yet much of the AI conversation in insurance remains focused on isolated administrative tasks. What insurers need is AI that carries connected workflows through to completion and strengthens every decision along the way, so they can move at the pace of the market while raising the bar on discipline.

Kalepa makes that possible by performing and orchestrating work across operations, underwriting, pricing, and portfolio management. The platform’s insurance-specific AI harness coordinates the agents behind those workflows, adapting as conditions change and matching the level of autonomy to each task and its risk. Teams step in where their expertise or approval is needed, and every result is verified so it can be traced and audited. That lets insurers rethink how work is split between AI and their people, so they can take on more business and strengthen risk selection.

Insurers using Kalepa have reported 30% to 60% more premium per underwriter, a 58% reduction in quote time, a 960-basis-point improvement in combined ratio, and double the quote-to-bind rate. The volume of work running through the platform grew 4x in the past year.

“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. “That means insurers can look at each task and ask who does it best, and at what cost. Sometimes that’s AI and sometimes it’s a person. When insurers get that division of labor right, their people’s attention can go to the complex risks, close calls, and broker relationships that need it. This funding lets us bring Professional Grade AI to more of the work insurers do, so they have that choice across the entire value chain.”

Kalepa has also added several senior leaders over the past year. Garrett Schlesinger most recently joined as Chief Technology Officer after 12 years at Affirm, where he was the company’s 12th employee and helped build its real-time underwriting system. Schlesinger joins Chief Revenue Officer David Meister, formerly of Addepar; Head of Product Audrey Howell, formerly of Palantir and Butterfly Network; and Head of Talent Tim Khoo-Jones, formerly Head of Talent at Block and Shopify.

Kalepa raised its last round, a $14 million Series A led by Inspired Capital with participation from IA Ventures, in 2021. The Series B was led by Updata Partners, with participation from IA Ventures and Inspired Capital. Kalepa has now raised $91 million in total.

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