Ledgebrook

Ledgebrook

Private
Boston, MassachusettsFinTechhttps://www.ledgebrook.com

Last Round

Series C

Jun 20, 2025

Total Funding Raised

$114.8M

Momentum Score

100 /100

Company Overview

Ledgebrook is an insurance technology company that modernizes specialty insurance through a technology-driven platform that streamlines quoting and risk assessment, allowing brokers to expedite deals and enhance client portfolios.

Sector

FinTech

Verticals

InsurTech, Compliance & Risk, Workflow Automation

Business Model

B2B

Customer Profile

Marketplace Commission, Services & Consulting

AI Layer

Application

Keywords

tech-enabled MGAExcess & Surplus insuranceE&S insuranceManaging General AgentMGAInsurTechspecialty insurancedigital MGAdata-driven underwritingwholesale insuranceGeneral LiabilityProfessional Liabilityinsurance quoting platformExcess Casualtyreinsurance broking

Historical Pricing

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Caplight Momentum Score

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Ledgebrook Comps

Public and private peers based on sector, stage, and business model.

CompanyStatusEst. ValuationRev Multiple
OpenAIPrivate$86.0B~40x
CoherePrivate$5.0B--
Competitor 1Public$XX.XBXXx
Competitor 2Public$XX.XBXXx

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Ledgebrook Funding Rounds

Historical fundraising activity

RoundDateAmount RaisedValuationInvestorsSources
Series CJun 20, 2025
Series BSep 12, 2024
Series AMar 28, 2024
SAFEApr 25, 2023
SeedAug 16, 2022

Key People

Founding team and executive leadership

Gage Caligaris

Founder CEO

Founding Team

Nathan Hall

Chief Technology Officer

Executive Team

Anthony Segal-Knowles

Chief Financial Officer

Executive Team

Adrian Copland

Chief Operating Officer

Executive Team

Ledgebrook Investors

Notable investors and investment history

InvestorRounds
Floating PointSeries A, Series C
Duquesne Family OfficeSeries B, Series C
StephensSeries B, Series C
The Stephens GroupSeries B, Series C
Hummingbird Nomads FundSeries C
Stephens Investment ManagementSeries B
MarkdSAFE

Market signals

Structured signals derived from secondary market and firmographic data.

  • Oct 1, 2025

    AI-Powered Copilot Chatbot to assist underwriters with document analysis.

  • Oct 1, 2025

    Operations recently expanded into the Polish market.

Ledgebrook Filings

SEC and related filings with document metadata.

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Ledgebrook Filings

SEC and related filings with document metadata.

Frequently Asked Questions

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Firmographic Details

HeadquartersBoston, Massachusetts
Employee Range183
Year Founded2021
Last FundingJun 20, 2025

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