Recent Funding
Founders
Gage Caligaris

Gage Caligaris

Founder ·

Largest round$200MLedgebrook · 2026

About Gage

Gage Caligaris is the founder and CEO of Ledgebrook, an AI-native specialty insurance platform based in Boston. He started his career trading commodity derivatives at Barclays before moving into insurance at Liberty Mutual, where he became a senior director. Caligaris founded Ledgebrook with the mission to provide faster and easier quoting experiences for wholesale brokers in the Excess and Surplus (E&S) market, combining insurance expertise with technology.

Strengths: founder archetype

Domain operatorQuant / trader

Domain operator 1

Quant / trader 1

Young outlier –

Capital allocator –

Technical builder –

Repeat founder –

Researcher –

Community builder –

one sourced signal · hover a cell for it, click for the source

Why domain operator

Gage Caligaris has a background in commodity derivatives trading and then spent significant time within the insurance industry, rising to a senior director role. This deep domain expertise in both finance and insurance, combined with his focus on leveraging technology and AI to solve industry pain points, positions him as a domain operator who is also a technical builder.

The signals behind it 2

Prior to entering insurance, Ledgebrook founder Caligaris traded commodity derivatives at Barclays.Quant / trader
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His insurance career started in the actuarial program at Liberty Mutual, where he rose to become senior director of new mobility products.Domain operator
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Network

Backed by 2

AAllianz XLed Ledgebrook's round, 2026

RRockefeller Capital ManagementLed Ledgebrook's round, 2026

GCGage Caligaris

Built and backed 1

LLedgebrookFounder

Background

Role Founder & CEO
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Previous Role Senior Director of New Mobility Products
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Previous Company Liberty Mutual
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Timeline, line by line 2

In their words

“The round recognizes the momentum in our business. It positions Ledgebrook to truly establish itself as a premier E&S platform, known for consistent execution on our mission to delight wholesale brokers and for bringing together the best of insurance expertise and technology”On Ledgebrook's Series C funding round and its mission. · Jun 25, 2025
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“The round recognizes the momentum in our business. It positions Ledgebrook to truly establish itself as a premier E + S platform, known for consistent execution on our mission to delight wholesale brokers and for bringing together the best of insurance expertise and technology. I am proud of the backing we have from our existing and new investors and am incredibly grateful for their support.”On the significance of the Series C funding round for Ledgebrook's position in the E+S market. · Jun 26, 2025
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Interviews and coverage

E&S Insurtech Ledgebrook Raises $65 MillionInsurance Journal · Jun 25, 2025
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Ledgebrook: $65 Million Series C Raised For Insurance Tech PlatformPulse 2.0 · Jun 26, 2025
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$17m Series B funding secured and Anthony Segal-Knowles named as CFO at LedgebrookReinsurance News · Oct 8, 2024
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Ledgebrook announces close of oversubscribed Series C Funding Round, led by existing investor Stephens GroupPR Newswire · Jun 24, 2025
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How this is researched

Researched from public pages: press, interviews, the company's site and the founder's own posts. Each source logo links the page that states the row; anything we couldn't source is left out. The archetype is our reading of that record, from a fixed set so founders can be compared. Updated Oct 12, 2026.