Kalepa Raises $75M Series B to Expand Insurance AI

The underwriter's afternoon has become part of Kalepa's commercial proposition. The insurance AI company wants software to do more of the work around evaluating a submission, leaving experienced people to decide where their attention earns its keep. That places a fairly human limit inside the ambition to process more insurance business: somebody still has to choose what deserves a closer look.

New York-based Kalepa announced a $75M Series B on November 5, 2026, at a $470M valuation. Updata Partners led the round, with IA Ventures and Inspired Capital participating, bringing total capital raised to $91M. The company plans to broaden its AI products, enter new markets and double headcount in 2027.

The financing arrives after Kalepa says it has spent more than 2 years cash-flow positive. Its opportunity is to carry software further into the work surrounding insurance decisions while preserving the judgment that makes those decisions commercially useful. For carriers evaluating AI, that puts the allocation of experienced attention close to the center of the purchase.

What Kalepa's Series B finances

Kalepa's previous financing was a $14M Series A in 2021, led by Inspired Capital with participation from IA Ventures. The company's account of that year describes work on complex commercial risks, APIs and integrations. The interval matters because the new capital follows several years of product development and customer relationships, giving returning investors an operating history against which to consider a larger commitment.

The company reports that revenue and customer count tripled over the past year. It has named W.R. Berkley, Bowhead Specialty and AmRisc among its customers, placing its software inside established insurance organizations. Absolute revenue, customer totals and audited financial statements were not disclosed in the announcement, so the growth figures describe company-reported progress rather than a complete financial picture.

Positive cash flow, on the company's account, changes the question around a financing of this size. Management can consider which adjacent work deserves investment, how quickly to recruit and how much organizational complexity to absorb. Kalepa's announced priorities give that choice a concrete shape: more products, more markets and a substantially larger team during 2027. The release supplies no detailed geographic rollout or allocation of proceeds, leaving those expansion decisions with management as the capital is deployed.

The insurer is buying a different use of attention

Kalepa describes its platform as coordinating insurance work across operations, underwriting, pricing and portfolio management. Those functions sit close together in a carrier's business, even when the information moves through separate systems and teams. A faster submission process creates value only when the next person or system can use what it produces, making the handoffs commercially significant.

In Church Mutual's deployment announcement, the company described reducing manual information gathering so underwriters could focus on the opportunities in front of them. That is a useful customer-level explanation of the purchase. The carrier is trying to direct experienced people toward decisions where their time has greater value, with software taking on more of the preparation around those decisions.

Kalepa's stated architecture assigns autonomy according to the task and its risk, with human expertise or approval retained where needed. A Finextra interview with CEO Paul Monasterio describes software reconciling applications with loss histories and escalating exceptions with supporting evidence. For an insurance buyer, that makes the quality of the escalation part of the product: someone still needs to understand why a file requires attention and what the underlying information supports. The commercial relationship therefore extends into how the carrier organizes the work around a quote.

A larger engineering organization inherits the handoffs

Kalepa was founded in 2018 by Paul Monasterio and Daniel Hillman, with Paul Monasterio serving as CEO. Its latest technology appointment brings experience from another business built around consequential financial decisions. Garrett Schlesinger became CTO in October after 12 years at Affirm, most recently as VP of Software Engineering, where his work included real-time underwriting systems.

Schlesinger's remit at Kalepa covers applied AI, research, engineering, data and infrastructure. The scope is revealing alongside the planned increase in headcount: extending a product into more insurance work also expands the engineering responsibility for how that work connects. A useful answer in one step has to remain useful when it reaches another workflow, a different insurance team or a decision requiring approval.

The company is also building around CRO David Meister, Head of Product Audrey Howell and Head of Talent Tim Khoo-Jones, whose appointments are identified in the funding release. Those roles put commercial expansion, product choices and recruitment alongside the technology assignment. Kalepa's careers page describes a remote-first team anchored by its New York headquarters, providing an existing organizational model for the planned hiring. Doubling that team is an intention for 2027, with the work of bringing new people into customer-facing delivery still ahead.

Insurance AI gets measured beyond the quote

The attraction of faster underwriting is easy to explain to a busy carrier. The economic consequence takes longer to observe, because the business also needs to understand which risks it selected, how those policies were priced and how the resulting portfolio performs. Software that touches several of those stages enters a broader customer conversation than a tool purchased for one administrative task.

Kalepa's funding release reports customer improvements in premium per underwriter, quote time and combined ratio. Those measures concern different parts of the insurance business, and the release does not provide the underlying cohort definitions or methodology needed to treat them as a universal benchmark. A buyer can use the reported outcomes to frame a more specific discussion about its own portfolio, operating process and definition of improvement.

That wider discussion gives Kalepa room to expand, and gives its customers more to decide. An insurer considering additional AI work has to determine where authority sits, how exceptions reach an expert and which information travels with them. As Kalepa recruits for its next stage, the next broker submission will keep making those choices concrete: a file enters the workflow, software does more of the preparation, and an underwriter has to recognize the business worth carrying.