Gage Caligaris
Founder & CEO
AI-native specialty (E&S) insurance platform for wholesale brokers
Ledgebrook is a Boston-based AI-native specialty insurance platform writing excess and surplus (E&S) lines for wholesale brokers, including general liability, professional liability and cyber insurance, plus a reinsurance arm, Ledgebrook Re. Its proprietary underwriting platform, Blackbird, is built for complex, hard-to-place commercial risks. It began writing business in 2023 and says it is on track to pass $1B in cumulative premium written. On October 7, 2026 it announced $200M in primary equity financing co-led by Allianz X and Rockefeller Capital Management, alongside a separate multi-year reinsurance agreement with Allianz Re (per Ledgebrook). The company was founded by CEO Gage Caligaris.
Founder & CEO