Kalepa Raises $75M to Scale Insurance AI

The big picture: Kalepa, a New York-based insurance AI startup, has closed a $75 million Series B round at a $470 million valuation, led by Updata Partners. The company reports being cash flow positive for over two years, having waited five years between funding rounds.

Why it matters:

• AI Dominance: This funding round comes as AI-focused companies captured 99.1% of insurtech funding in Q2 2026, highlighting the industry’s shift towards AI-driven solutions.
• Operational Efficiency: Kalepa’s software significantly improves key insurance metrics, with users reporting over 58% higher premium per underwriter, 30-60% faster quote delivery, and a 9.6 percentage point reduction in combined ratio.
• Strategic Growth: The capital will fuel Kalepa’s expansion of its AI product offerings, entry into new markets, and a planned doubling of its team by 2027, positioning it for continued growth in a rapidly evolving sector.

How it works:

• Underwriting Automation: Kalepa’s platform assists insurers, MGAs, reinsurers, and program administrators with underwriting, pricing, and portfolio management decisions across more than 10 countries.
• Professional Grade AI: The system utilizes dedicated software to orient AI agents for multi-step tasks, while maintaining human oversight for complex or high-risk decisions, ensuring traceability and auditability.
• Integrated Workflow: For underwriters, Kalepa consolidates research, data, and guidelines into a single workspace, flagging information gaps and streamlining the policy submission process, as demonstrated in case studies with clients like Bowhead Specialty.

The catch: The insurance AI market is increasingly crowded, with rivals like Federato, Six, and Artificial Labs also securing substantial funding for their underwriting platforms. While Kalepa emphasizes ‘Professional Grade AI’ that integrates human judgment and audit trails, competitors like Sixfold advocate for end-to-end autonomous underwriting. If the market shifts towards greater agent autonomy with less human supervision, Kalepa’s model, which values human oversight at every stage, could face pressure to adapt or risk losing its competitive edge, despite the projected $30.07 billion growth in AI in the insurance market by 2029.

Key Facts

• Company: Kalepa
• Amount: $75M
• Round: Series B
• Investors: Updata Partners (lead), IA Ventures, Inspired Capital
• Founders: Paul Monasterio, Daniel Hillman
• Valuation: $470,000,000
• Sector: Insurance AI
• Headquarters: New York, US