Ledgebrook is a Boston-based AI-native specialty insurance platform for mid-sized businesses with complex, hard-to-place risks. Writing general liability, professional liability and specialty coverage in the excess and surplus (E&S) market, it distributes exclusively through wholesale brokers, with its proprietary Blackbird platform reading submissions, classifying risk and calculating technical prices so experienced underwriters can quote in hours rather than weeks. Founded in 2022 by Gage Caligaris, the company completed its transition to a full-stack carrier after its insurance subsidiary received an A- (Excellent) rating from AM Best in August 2026, employs around 300 people, and has been on track to surpass $1 billion in cumulative premium written since it started writing business in 2023.
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Oct 7, 2026
Latest raise
Funding activity · 1 round
Oct 7, 2026
$200M
Series C+
Led by Allianz X
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