Kalepa Raises $75 Million Series B at $470 Million Valuation to Expand AI-Powered Insurance Underwriting

New York-based insurance technology startup Kalepa has raised $75 million in a Series B funding round at a $470 million valuation, five years after its previous institutional funding round.

The investment was led by Updata Partners, with participation from returning investors IA Ventures and Inspired Capital. The company also counts several prominent individual backers, including former US Commerce Secretary Penny Pritzker, Carta CEO Henry Ward, Lead Bank CEO Jacqueline Reses and investor Gokul Rajaram.

Founded by Paul Monasterio and Daniel Hillman, Kalepa develops AI-powered software for insurers, managing general agents (MGAs), reinsurers and programme administrators. Its platform supports underwriting, pricing and portfolio management decisions.

The company says it has been cash flow positive for more than two years and operates in over 10 countries. It plans to use the new funding to expand its AI product offering, enter additional markets and double its team by 2027.

From Nuclear Science to Insurance Technology

Kalepa was founded by Paul Monasterio and Daniel Hillman, who brought experience in analytics and technology to the insurance industry.

Monasterio holds a PhD in nuclear science and engineering from the Massachusetts Institute of Technology (MIT). Before launching Kalepa, he worked at Applied Predictive Technologies, an analytics company acquired by Mastercard for $600 million in 2015. He subsequently held roles at Mastercard and Facebook.

Hillman also built his career at Applied Predictive Technologies and Mastercard, progressing through sales roles before co-founding Kalepa.

The founders identified an opportunity to apply advanced analytics and automation to commercial insurance underwriting, where decisions often require reviewing complex submissions, assessing risks and coordinating large amounts of information.

AI Agents for Insurance Underwriting and Portfolio Management

Kalepa's platform is designed to coordinate workflows across insurance operations, including underwriting, pricing and portfolio management.

Its AI agents can carry out multi-step tasks, bringing together relevant research, data and underwriting guidelines. The platform adjusts the level of automation according to the complexity and risk associated with each task.

Human professionals remain involved when specialist judgment or approval is required. Kalepa also emphasises traceability and auditability, allowing insurers to review how decisions and actions were handled.

For example, when an underwriter receives a new policy submission from a broker, the platform can consolidate research, relevant data and underwriting guidelines into a single workspace. It can also identify missing information that may be needed before the risk can be assessed.

This approach is intended to reduce administrative work while keeping experienced underwriters involved in decisions that require human expertise.

Reported Improvements in Underwriting Performance

Kalepa says insurers using its platform have reported improvements in several operational metrics.

According to the company, customers have achieved:

• More than 58% higher premium per underwriter.

• Quotes delivered 30-60% faster.

• A 960-basis-point improvement in combined ratio, equivalent to a 9.6-percentage-point reduction in the proportion of premiums spent on claims and expenses.

These are company-reported customer outcomes. They indicate the types of efficiency and profitability improvements Kalepa aims to support, but the source does not provide independently audited results across its entire customer base.

A $75 Million Round After Five Years

Kalepa's latest investment follows its $14 million Series A round in 2021, led by Inspired Capital.

The five-year gap between the two rounds is notable, particularly as the company reports having remained cash flow positive for more than two years.

With the Series B, Kalepa says its total funding has reached $91 million.

Updata Partners led the latest round, while IA Ventures and Inspired Capital returned as investors. The company plans to direct the capital towards product development, geographic expansion and hiring.

Its target is to double its team by 2027.

Competition in AI-Powered Insurance Underwriting

Kalepa operates in a growing market for AI applications in insurance, particularly in commercial underwriting.

Competitors include Federato, which raised $100 million in a Series D in November 2025, Sixfold, which raised $30 million in a Series B in January 2026, and London's Artificial Labs, which raised $45 million for its digital underwriting software.

While these companies are developing AI-based underwriting solutions, Kalepa emphasises a task-specific approach to automation.

Rather than positioning AI as a complete replacement for underwriters, the company argues that different tasks require different levels of autonomy. AI can handle suitable workflows, while people remain responsible for decisions that need professional judgment and approval.

What Comes Next for Kalepa?

With a $470 million valuation and $75 million in new capital, Kalepa is preparing for its next stage of expansion.

The company intends to broaden its AI product capabilities, enter new markets and double its workforce by 2027.

Its longer-term opportunity depends on whether insurers continue adopting AI systems that combine workflow automation with human oversight, particularly in complex commercial insurance operations.

Kalepa's ability to demonstrate reliable results, maintain customer trust and scale across international markets will shape its position in the increasingly competitive insurance AI sector.