About Ledgebrook
Ledgebrook is a Financial Services company based in Boston (United States) founded in 2021 by Gage Caligaris. It operates as an insurance underwriting research solutions are provided to brokers. Ledgebrook has raised $314.8 million across 6 funding rounds from investors including Floating Point, The Stephens Group and Brand Foundry. Its chief executive is Gage Caligaris. Its focus areas include FinTech, Insurance IT, Insurance Policy Solutions and Software for Insurance Intermediaries. Its legal entity is Ledgebrook Insurance LLC. Its competitors include Joyn Insurance, Optio Group, Insurance Quantified, elseco and BondCenter and 4 more; 3 of its 9 listed competitors have raised funding.
Company details
Ledgebrook was founded in 2021 and is based in Boston, United States. Operations focus on the insurance sector, where data-driven underwriting tools are developed for brokers. Services encompass streamlined submission processes, reduced time to quote, and a cloud-based digital workflow. Integration with data science is utilized to enhance efficiency across end-to-end operations.
- Headquarters Boston, United States
- Founders Gage Caligaris
- SectorsFinancial Services
- Email••••••••
- Website ledgebrook.com
- Social LinkedIn X
- Legal Name Ledgebrook Insurance Llc
- Total Equity Funding$314.8M (USD)
in 6 rounds
- Latest Funding Round$200M (USD), Series D
Oct 2026
- InvestorsFloating Point
& 8 more
Funding Insights of Ledgebrook
Ledgebrook has successfully raised a total of $314.8M across 6 strategic funding rounds. The most recent funding activity was a Series D round of $200 million completed in October 2026. This substantial capital infusion reflects strong investor confidence in the company's business model, growth potential, and market opportunities. The funding enables strategic expansion, product development, market penetration, and operational scaling to drive long-term value creation and competitive advantage.
- Total Funding $314.8M
- Total Rounds 6
- Last Round Series D — $200M
- First Round $4.2M
(Apr 2022)
- Investors Count 9
All 6 funding rounds of Ledgebrook with amounts and investors; the two latest post-money valuations are shown, the rest are part of the premium plan.
| Date | Amount | Transaction Name | Valuation | Lead Investors | Investors |
|---|---|---|---|---|---|
| Oct 2026 | $200M | Series D | – | Allianz X, Rockefeller Capital Management | – |
| Jun 2025 | $65M | Series C | – | The Stephens Group | |
| Sep 2024 | $17M | Series B | – | The Stephens Group, Brand Foundry | – |
| Mar 2024 | $24M | Series A | – | – | – |
| Apr 2023 | $4.6M | Seed | – | Brand Foundry, American Family Ventures | – |
| Apr 2022 | $4.2M | Seed | – | Brand Foundry |
9 investors in total: 9 institutional.
Investors in Ledgebrook
Ledgebrook has secured backing from 9 investors, including venture fund and institutional investors. Prominent investors backing the company include Floating Point, The Stephens Group and Brand Foundry.
| Investor | Description | Founded Year | Domain | Location |
|---|---|---|---|---|
Private equity firm focused on multiple sectors | – | stephensgroup.com | Little Rock, United States | |
Venture capital fund investing in early-stage tech startups | – | brandfoundry.com | Austin, United States | |
Corporate-backed venture capital firm focused on fintech, Insurtech, and multiple sectors | – | amfamventures.com | Madison, United States | |
- | – | duquesnefamilyofficellc.tcc.mode | - | |
Venture capital fund focused on tech companies | 2019 | floating.vc | New York, United States | |
Investments in early-stage startups are focused on by Hummingbird Ventures. | – | hummingbird.vc | London, United Kingdom | |
- | – | allianzx.com | - | |
Delivers comprehensive fund, financial, and investment advisory services. | 2000 | duquesne.com | Pittsburgh, United States | |
- | – | rockco.com | - |
Investor details for Ledgebrook
The complete investor list, round-by-round participation and investor portfolios require an active premium plan.
- Complete investor list
- Round participation
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People of Ledgebrook
22 people are tracked at Ledgebrook (12 in leadership, 10 in team).
| Name | Role | Group |
|---|---|---|
Gage Caligaris | Founder & CEO | Leadership |
Ryan Morrow | Managing Director | Leadership |
Steve Mills | President, E&S | Leadership |
John Mullen | Chief Underwriting Officer, General Liability | Leadership |
James Lassiter, RPLU, CPLP | Vice President - Head of Professional Liability | Leadership |
Aleksandra Tyler | Chief of Staff | Leadership |
Adrian Copland | Chief Operating Officer | Leadership |
Jeff Snook | VP Actuarial | Leadership |
Paul Velekei | Chief Operating Officer | Leadership |
Nathan Hall | CTO | Leadership |
Erik Soria | Head Of Strategy | Leadership |
Troy Guerrero | VP Head Of Excess Casualty | Leadership |
Stacy Vasilatos | Executive Assistant | Team |
Carter Bishop | Senior Underwriter | Team |
Nicholas Cheung | Underwriter | Team |
Pamela Okechukwu | Underwriting Assistant | Team |
Damian Jaskulski | Associate Underwriter | Team |
Nicolette Oster | Senior Underwriter | Team |
Ashton E. | Underwriting Assistant | Team |
Craig Lewis | Senior Operations Manager | Team |
2 more people are available in the full profile.
Complete people profiles for Ledgebrook
Full employee and board profiles, team structure, tenure and professional contact details require an active premium plan.
- Full employee list
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Verified entity values are shown only after access is granted.
Timeline of Ledgebrook
3 dated milestones of Ledgebrook across 5 years, from founding to its latest funding, stage changes and deals.
- Founded Ledgebrook is founded.
- Funding First funding round of $4.2M.
- Funding Latest funding round, Series D, of $200.0M.
Competitors of Ledgebrook
Ledgebrook has 9 listed competitors in our database, 3 of them funded. They include Joyn Insurance, Optio Group, Insurance Quantified, elseco and BondCenter, among others.
| Company Name | Domain | Founded | HQ Location | Total funding | Employees | Description |
|---|---|---|---|---|---|---|
| joyninsurance.com | 2020 | New York, United States | $17.7M | – | Provider of insurance underwriting services | |
| optiogroup.com | 2011 | London, United Kingdom | – | – | Claims consulting and insurance underwriting services are provided. | |
| insurancequantified.com | 2017 | Ann Arbor, United States | – | – | Offers AI-powered data ingestion and analytics for property and casualty underwriting. | |
| else.co | 2006 | Dubai, United Arab Emirates | – | – | Insurance underwriting services are provided in Dubai. | |
| bondcenter.com | 2022 | Austin, United States | $500,000 | – | Offers an automated bonding solution tailored for insurance agents. | |
| favershamunderwriting.com | 2013 | London, United Kingdom | – | 4 | Online insurance underwriting solutions are provided to brokers. | |
| aurenity.com | 2022 | West Hartford, United States | – | – | Offers excess and surplus insurance via brokers, partnerships, and technology expertise. | |
| qubituw.com | 2023 | Hong Kong, China | – | – | Insurance products for digital assets are underwritten by Qubit. | |
| findevor.ai | 2024 | New York, United States | $500,000 | – | AI-based data analyst platform is developed for investment optimization. |
Detailed competitors of Ledgebrook
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- Full competitor set
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Web traffic of Ledgebrook
The website of Ledgebrook (ledgebrook.com) receives about 4.6K visits a month.
- Monthly visits4.6K
▲ 12.1% vs previous month
Top companies in Insurance Technology & Support Services
10 companies that operate in the same segment as Ledgebrook (Insurance Technology & Support Services), ranked by their profile score on The Company Check.
| Company | Description | Founded | Location | Total funding | Revenue | Employees |
|---|---|---|---|---|---|---|
Insurance products for vehicles, health, travel, and life are offered. | 2016 | Bengaluru, Karnataka, India | USD 746.17 M | USD 216.04 M | 1,306 | |
Auto insurance is delivered via app to individual drivers. | 2017 | London, England, United Kingdom | USD 161.3 M | USD 369.88 M | 625 | |
Cloud-based platform for property and casualty insurance is provided. | 2001 | San Mateo, California, United States | – | USD 1.48 B | 226 | |
Claims administration, loss adjusting, and benefits management services are provided. | 1969 | Memphis, Tennessee, United States | USD 2.63 M | – | – | |
Online property and casualty insurance is provided for businesses. | 2017 | San Francisco, California, United States | USD 800 M | – | 699 | |
Satellite-based imaging solutions are provided using synthetic aperture radar. | 2016 | Palo Alto, California, United States | USD 233.99 M | – | 191 | |
API-enabled insurance distribution platform is provided for B2C companies. | 2011 | Noida, Uttar Pradesh, India | USD 120.6 M | – | – | |
AI and microsatellite-based imaging solutions are developed for data monitoring. | 2014 | Espoo, Uusimaa, Finland | USD 1.25 B | USD 111.51 M | 1,156 | |
Software suite for insurance distribution and management is provided. | 2014 | New York, New York, United States | USD 354.55 M | USD 21.6 K | 649 | |
AI-enabled driver monitoring and fleet safety management solutions | 2015 | Palo Alto, California, United States | USD 215 M | – | 109 |
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Frequently Asked Questions about Ledgebrook
Ledgebrook was founded in 2021 and raised its 1st funding round 1 year after it was founded.
Ledgebrook is headquartered in Boston, United States. It is registered at Boston, Massachusetts, United States.
Gage Caligaris is the current CEO of Ledgebrook. They have also founded this company.
Ledgebrook is a funded company, having raised a total of $314.8M across 6 funding rounds to date. The company's 1st funding round was a Seed of $4.2M, raised on Apr 2022.
Ledgebrook was founded in 2021 and is based in Boston, United States. Operations focus on the insurance sector, where data-driven underwriting tools are developed for brokers. Services encompass streamlined submission processes, reduced time to quote, and a cloud-based digital workflow. Integration with data science is utilized to enhance efficiency across end-to-end operations.
Ledgebrook's top competitors include Joyn Insurance, Qubit and Optio Group.
Ledgebrook has 9 investors. Key investors include Floating Point, The Stephens Group, Brand Foundry, American Family Ventures, and Duquesne Family Office.
Ledgebrook operates through Ledgebrook Insurance Llc.