Kalepa raises $75 million at $470 million valuation to expand insurance AI

Kalepa’s previous round was a $14 million Series A in 2021, led by Inspired Capital with IA Ventures participating. The new financing brings total funding to $91 million. Kalepa says revenue and customer numbers each tripled over the past year, while the volume of work on its platform grew fourfold.

The announcement gives no absolute revenue or customer count and does not define a unit of platform work, limiting what those growth rates reveal about its scale or valuation against sales. Named customers include insurers W.R. Berkley and Bowhead Specialty, and managing general agent AmRisc.

Monasterio said most hiring would be in engineering, AI and commercial roles, in an interview carried in the funding report. Kalepa plans to double headcount in 2027 but did not give the starting workforce in its announcement.

Monasterio also said Kalepa plans to open a London office in the coming months, according to the report’s accessible preview. Kalepa already supports London-based managing general agents, so the proposed office would build on an existing customer presence.

Paul Monasterio, Kalepa’s co-founder and CEO. Photo: Kalepa. Source: Kalepa.

Insurers decide how much authority to delegate

In a separate interview, Monasterio said Kalepa can reconcile applications with loss histories, flag missing or inconsistent information and apply an insurer’s underwriting and pricing rules. He said agents can determine whether a broker submission fits an insurer’s risk appetite, prioritize opportunities and prepare quotes within authority granted by the insurer.

In that account, risks within established guidelines can proceed without an underwriter checking every step, while exceptions are escalated with supporting evidence. Kalepa says its system coordinates AI models and deterministic software, checks outputs, and retains evidence and reasoning for audit. Those are company descriptions of the controls, rather than independent verification of their effectiveness.

The company’s August technical explanation says unusual accounts with conflicting documents or missing information may require more validation and earlier human involvement. Automation therefore depends on the task and available evidence, rather than applying equally to every submission.

Monasterio said many consequential decisions currently work best when AI performs the work and a person decides; greater autonomy depends on demonstrated reliability. He also emphasized people’s role in close calls and broker relationships.

Kalepa has hired Garrett Schlesinger as chief technology officer after 12 years at Affirm, where he helped build its real-time underwriting system, according to the funding announcement.

The evidence insurers need before delegating more

Kalepa says insurers using its software have reported 30% to 60% more premium per underwriter, a 58% reduction in quote time, a 960-basis-point improvement in combined ratio and twice the quote-to-bind rate. These measure different outcomes: premium volume per employee, speed, underwriting profitability and conversion from quotes to policies. More premium per underwriter alone does not establish more profitable business.

The combined-ratio claim amounts to a 9.6-percentage-point improvement, not a 9.6% relative change. But the announcement provides no starting ratios, customer sample sizes, measurement periods or method for isolating the software’s contribution. It does not establish that all the gains occurred at the same insurers. The figures cannot establish a typical customer result or be combined into a single return-on-investment estimate.

As Kalepa expands its products, the next decision for insurers is which additional tasks warrant delegated authority. That requires results by insurance business, software and integration costs, and evidence of how often staff must intervene or correct a decision. The financing gives Kalepa resources to expand; the published figures do not yet show the economics of granting its agents more responsibility.

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