Ledgebrook Named to the 2026 CB Insights’ 50 Most Promising Insurtech Startups

Ledgebrook named among the world's most promising insurtechs for bringing insurance judgment and technology built from scratch to specialty risk, broker-first from day one.

NEW YORK, September 24, 2026 — CB Insights today named Ledgebrook to its fifth annual Insurtech 50, showcasing the 50 most promising insurtech startups in the world.

"The 2026 Insurtech 50 reveals the top startups shaking up the insurance industry's status quo," said Chris Sekerak, Lead Analyst at CB Insights. "The common thread across the cohort is the ability to scale differentiated businesses that are unlikely to be displaced by large AI or insurance companies."

“This recognition reflects what happens when insurance judgment and technology built from scratch work hand in hand. What matters most is what that means for our brokers and the risks they trust us to underwrite.”
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- Chris Sekerak, Lead Analyst at CB Insights

Gage Caligaris, Founder & CEO

The list includes 27 insurers and intermediaries, and 23 tech vendors. Our research team picked winning companies based on CB Insights datasets, including deal activity, industry partnerships, team strength, investor strength, executive interviews, and proprietary metrics.

Ledgebrook is an AI-native specialty insurance platform. It sits between the brokers who need coverage for custom and complex risks and the capital that backs them, running on technology built from scratch. Founded in Boston in 2022 by Gage Caligaris, a Harvard mathematician and actuary, Ledgebrook writes general liability, professional liability and specialty coverage through wholesale brokers. The company employs around 300 people, including some 80 underwriters and 50 engineers, and is approaching $1 billion in premium written since inception. Both of its rated carriers hold an A- (Excellent) from AM Best, with a stable outlook.

Quick facts on the 2026 Insurtech 50:

• Raised $3.0B in equity funding over time, including more than $0.8B in 2026 so far (16% of YTD insurtech funding).

• Disclosed 70+ partnerships since 2025, including with industry leaders like ADP, Marsh, and Sun Life.

• Includes 31 early-stage startups, 14 of which are at the seed stage.

• Employs 5,400+ people, with a median headcount of 52 across the cohort.

• Ranks among the top 4% of private companies globally for overall health and growth potential.

About CB Insights

CB Insights spots winners in emerging tech. Since 2008, we've ranked and rated the private companies reshaping their industries, drawing on proprietary interviews with operators and deep, validated intelligence on over 12 million companies. We give decision-makers an edge by enriching their AI agents with a complete map of technology markets, nonpublic data, and expert judgment. Six of the Mag 7 and 26 of the 30 largest banks rely on CB Insights to build conviction in their next investment, acquisition, partner, or customer.

Learn more at www.cbinsights.com for more information.

Contact

Media@cbinsights.com

About Ledgebrook

To learn more about Ledgebrook and opportunities to join our team, please visit www.ledgebrook.com or email info@ledgebrook.com.