Kalepa Raises $75M for AI Agents Across Insurance Operations

By Grace Kim

Kalepa raised $75 million in a Series B at a $470 million valuation, bringing total funding to $91 million, CEO and founder Paul Monasterio told AlleyWatch.

Updata Partners led the round, with continued support from longtime investors IA Ventures and Inspired Capital, Monasterio said.

He said Kalepa tripled revenue and customer count over the past year while the volume of work on its platform grew fourfold.

Monasterio said customer deployments show a 960-basis-point improvement in combined ratio, 58% faster quotes and 30%-60% higher premium per underwriter.

Kalepa has remained cash-flow positive for more than two years and has not raised capital since 2021, he added.

Monasterio said: “It is unusual to find rapid growth, exceptional customer retention and expansion, financial discipline, and a massive market opportunity in the same business.”

What does Kalepa’s platform do?

Kalepa calls its offering Professional Grade AI for insurance. Its agents perform and coordinate work across underwriting, operations, pricing and portfolio management rather than automating one step at a time, Monasterio said.

The platform matches autonomy to each task and insurer requirement. It brings people in where expertise or approval is needed and verifies every result so insurers can trace and audit it, he said.

Monasterio said insurance decisions can carry consequences for years, so auditability and trust must be built in.

Customers include global insurance group W.R. Berkley, specialty insurer Bowhead Specialty and managing general agent AmRisc, which underwrites on behalf of insurers. Monasterio said customers such as these expanded their use of Kalepa over the past year.

Kalepa says retiring veteran underwriters take decades of pricing judgment with them, just as rising losses and softening prices narrow the margin for error and AI-native competitors enter.

The company says most insurers still apply AI to isolated administrative tasks rather than core decisions on which risks to write and how to price them.

Kalepa is aiming at decisions that set premiums and portfolios, not just back-office work.

How did Kalepa build its technology?

Monasterio and co-founder Danny Hillman previously worked with insurers at Applied Predictive Technologies, where they saw consequential decisions made with fragmented information and substantial manual work.

Monasterio said insurance enables business investment and innovation, including coverage for AI and commercial space.

They founded Kalepa in New York in 2018 around the conviction that AI could improve how insurers understand and underwrite risk.

Monasterio said Kalepa spent years on entity resolution, determining which business, person or asset information refers to the same entity, and on applying transformer architecture to risk outcomes.

Reliable execution also requires coordinating complex workflows and producing consistent work at the level expected of experienced insurance professionals, he said.

Those pieces give Kalepa a foundation for taking on multi-step insurance work.

How does Kalepa make money?

Kalepa uses value-based pricing. Insurers pay in proportion to the book of business it supports and the outcomes it delivers, Monasterio said.

He said customer relationships expand as insurers deploy the platform across more teams, lines of business and workflows.

The company initially targets property and casualty insurance in the $7 trillion global insurance market and aims to extend across the full value chain, he said.

Monasterio said: “We intend for Kalepa to become the core platform through which insurers run their businesses.”

He expects advances in AI to expand the scope and complexity of work Kalepa can handle.

Value-based pricing links Kalepa’s revenue directly to the insurance business it supports.

Why did investors fund the round?

Monasterio said advances in AI and insurer demand expanded the opportunity and made this the right time to raise.

He described the financing process as relatively straightforward because Kalepa had built technology in production, delivered results and grown efficiently.

The harder choice was finding an investor for a partnership that could last years. He said Updata understood the opportunity and the operating discipline behind Kalepa.

Monasterio said Kalepa’s cash generation gives it flexibility, while the new capital lets it invest more aggressively without abandoning financial discipline.

Monasterio said pressure on growth and profitability in a slowdown increases the value of evaluating more opportunities, selecting business and reducing the work needed to serve it.

The round adds capital without reversing the discipline that built the business.

What changes in the next six months?

Over the next six months, Kalepa plans to widen both the work it performs and the number of insurers it serves, Monasterio said.

Product plans include more complex workflows and connections among underwriting, operations, pricing and portfolio management.

Commercial plans include broader deployments with existing customers, new customer relationships and further expansion in Europe, he said.

Kalepa has hired senior leaders with experience at Affirm, Addepar, Palantir, Block and Shopify, and is adding engineering, AI and commercial talent.

Monasterio said the company plans to double headcount in 2027 but will judge that expansion by what the team delivers for customers.

Expansion now depends on turning broader capabilities into more insurer deployments.

What advice does Monasterio give?

Asked how New York technology companies without fresh capital should proceed, Monasterio said to invest in the product and in tangible, demonstrable customer impact.

He warned that heavy sales and marketing spending before product-market fit can make growth figures look good temporarily while masking weak underlying economics.

Insurance offers a stark example, he said: companies can grow quickly by writing business with poor economics, only for eventual losses to become catastrophic.

The new capital will fund product development, hiring and international expansion. He expects Kalepa to take a larger role in insurer operations while preserving the control and reliability customers require.

The next test is whether Kalepa can convert its reported gains into wider deployments across underwriting, pricing and portfolio management.