Kalepa Raises $75 Million in Series B at $470 Million Valuation
Key Takeaways
- •Kalepa raised $75 million in Series B funding at a $470 million valuation, led by Updata Partners with participation from IA Ventures and Inspired Capital, bringing its total funding to $91 million.
- •The company tripled both revenue and customer count over the past year while staying cash-flow positive for more than two years.
- •Kalepa intends to use the new capital to expand its AI product suite, enter new markets, and double its headcount in 2027.
- •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 a doubled quote-to-bind rate.
- •Garrett Schlesinger joined as chief technology officer after 12 years at Affirm, part of an expanded senior leadership team at Kalepa over the past year.

Kalepa, which provides Professional Grade AI for insurance, has announced $75 million in Series B funding at a $470 million valuation. Over the past year, the company has tripled both its revenue and customer count while remaining cash-flow positive for more than two years.
Kalepa said it will use the new capital to expand its AI product suite, enter new markets and double its headcount in 2027 — the only one of those plans with a date attached. Its customers include major insurers and managing general agents (MGAs) — firms that insurers authorize to underwrite and service policies on their behalf — including W.R. Berkley, Bowhead Specialty and AmRisc.
The insurance industry is facing pressure from rising losses, the retirement of experienced professionals and the arrival of AI-native competitors designed for speed. At the same time, softer pricing is leaving less room for error in underwriting and other decisions. Kalepa said much of the insurance AI market remains focused on individual administrative tasks, while insurers need systems that can carry connected workflows through to completion and support decision-making across the organization.
Kalepa’s platform performs and coordinates work across operations, underwriting, pricing and portfolio management. Its insurance-specific AI harness coordinates the agents supporting those workflows, adapts as conditions change and adjusts the level of autonomy according to each task and its risk. Employees can intervene when their expertise or approval is required, while each result is verified for traceability and auditing.
The company said this approach allows insurers to reconsider how work is divided between AI and employees, enabling them to handle more business and improve 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 — the industry’s core underwriting gauge, which weighs claims and expenses against premiums, where a basis point is one-hundredth of a percentage point and a lower reading is better — and a doubling of the quote-to-bind rate, the share of quoted risks that turn into bound, or issued, policies. The volume of work processed through the platform increased 4x over 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 expanded its senior leadership team over the past year. Garrett Schlesinger 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. He 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.
The company’s previous financing was a $14 million Series A led by Inspired Capital, with participation from IA Ventures, in 2021. Updata Partners led the Series B, which also included IA Ventures and Inspired Capital. Kalepa has raised $91 million in total.