# Gage Caligaris

> Gage Caligaris is the founder and CEO of Ledgebrook, a tech-enabled managing general agent (MGA) modernizing the Excess and Surplus (E&S) specialty insurance market. A Harvard-trained applied mathematician and former Barclays commodity derivatives trader, he spent eight-plus years as an actuary at Liberty Mutual, where he became the fastest person ever to pass the Casualty Actuarial exams and later scaled a new-mobility products line from under $50M to over $450M in gross written premium. He founded Ledgebrook in 2022 to pair modern engineering with deep insurance expertise, reaching a $100M run rate in under two years and raising an oversubscribed $65M Series C in 2025. In 2026 he was named an EY Entrepreneur Of The Year New England Award winner.

- **Role:** Founder & CEO at Ledgebrook
- **Organizations:** Ledgebrook, Liberty Mutual (former), Barclays (former)
- **Nationality:** American
- **Education:** Degree in Applied Mathematics, Harvard University
- **Known for:** Founded Ledgebrook and scaled it to a $100M run rate in under two years, Raised an oversubscribed $65M Series C in 2025, bringing total funding past $110M, Became the fastest person ever to pass the Casualty Actuarial exams at Liberty Mutual

## Career timeline

- **Early career** — Traded exotic commodity derivatives as a proprietary trader at Barclays
- **~2013-2022** — Joined Liberty Mutual's actuarial program; became the fastest person ever to pass the Casualty Actuarial exams
- **At Liberty Mutual** — Led pricing teams across Auto, Homeowners, General Liability, Umbrella and Excess lines
- **At Liberty Mutual** — As Senior Director of New Mobility Products, grew a line from under $50M to over $450M in gross written premium
- **2022** — Founded Ledgebrook, a tech-enabled E&S specialty insurance MGA
- **2022** — Closed $24M Series A led by American Family Ventures
- **2024** — Reached a $100M run rate in under two years after writing the first policy
- **2025** — Closed an oversubscribed $65M Series C led by The Stephens Group; total funding surpassed $110M
- **2026** — Named EY Entrepreneur Of The Year New England Award winner

## Achievements

- Founded Ledgebrook and scaled it to a $100M run rate in under two years
- Raised an oversubscribed $65M Series C in 2025, bringing total funding past $110M
- Became the fastest person ever to pass the Casualty Actuarial exams at Liberty Mutual
- Grew a Liberty Mutual new-mobility line from under $50M to over $450M in GWP
- Named 2026 EY Entrepreneur Of The Year New England Award winner
- Holds FCAS (Fellow of the Casualty Actuarial Society), CFA and CPCU designations

## Latest updates

- **2025-06** — Ledgebrook closed an oversubscribed $65M Series C led by The Stephens Group; total funding surpassed $110M.
- **2026** — Named EY Entrepreneur Of The Year New England Award winner.

## Links

- Website: https://ledgebrook.com
- LinkedIn: http://www.linkedin.com/in/gage-caligaris-fcas-366a9b21
- Twitter/X: https://twitter.com/ledgebrook_inc
- Facebook: https://facebook.com/LedgebrookInsurance/

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Profile page: https://yespress.io/gage-caligaris
Published by YesPress — https://yespress.io
Last updated: 2026-07-17