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Ledgebrook

Ledgebrook

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

Last Round

Series C

Jun 20, 2025

Total Funding Raised

$114.8M

Momentum

Top 25%

of companies Caplight tracks

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

Business Model

B2B

Customer Profile

Marketplace Commission, Services & Consulting

AI Layer

Application

Keywords

insurtechMGAmanaging general agentE&S insuranceexcess and surplusunderwriting platformreinsurancedigital MGAinsurance automationrisk assessmentwholesale insurancequote-to-bindinsurance capacityunderwriting workflowinsurance software

Historical Pricing

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Caplight Momentum Score

Proprietary index based on bid/ask volume and sentiment.

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Ledgebrook Comps

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

Ledgebrook comps — public and private peers by 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

Data table
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

Ledgebrook investors
InvestorRounds
Floating PointSeries A, Series C
Duquesne Family OfficeSeries B, Series C
StephensSeries B, Series C
Floating Point AdvisorsSeries A, Series C
The Stephens GroupSeries B, Series C
NomadsSeries C
Stephens Investment ManagementSeries B

Market signals

Structured signals derived from secondary market and firmographic data.

  • Jun 18, 2026

    Grew 17% QoQ, from 195 to 228 employees.

  • Oct 1, 2025

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

Ledgebrook Filings

SEC and related filings with document metadata.

Data table
TypedDateAmount OfferedAmount SoldFillingPagesDownload
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Ledgebrook Filings

SEC and related filings with document metadata.

Frequently Asked Questions

Common questions about Ledgebrook's valuation, stock price, and market status.

Firmographic Details

HeadquartersBoston, Massachusetts
Employee Range228
Year Founded2021
Last FundingJun 20, 2025

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