About Ledgebrook
Ledgebrook is a company based in Boston (United States) founded in 2021 by Gage Caligaris.. Ledgebrook has raised $114.8 million across 5 funding rounds from investors including Floating Point, The Stephens Group and Brand Foundry. Ledgebrook operates in a competitive market with competitors including Joyn Insurance, Optio Group, Insurance Quantified, elseco and BondCenter, among others.
- Headquarter Boston, United States
- Founders Gage Caligaris
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Sectors
Financial Services
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Email
***********
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Phone
*********
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Website
*********
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Social
*********
- Legal Name Ledgebrook Insurance Llc
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Annual Revenue
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Net Profit
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EBITDA
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Total Equity Funding
$114.8 M (USD)
in 5 rounds
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Latest Funding Round
$65 M (USD), Series C
Jun 24, 2025
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Investors
Floating Point
& 6 more
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Employee Count
Employee Count
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Funding Insights of Ledgebrook
Ledgebrook has successfully raised a total of $114.8M across 5 strategic funding rounds. The most recent funding activity was a Series C round of $65 million completed in June 2025. 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 Total Funding
- Total Rounds 5
- Last Round Series C — $65.0M
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First Round
First Round
(25 Apr 2022)
- Investors Count 7
| Date | Amount | Transaction Name | Valuation | Lead Investors | Investors |
|---|---|---|---|---|---|
| Jun, 2025 | Amount | Series C - Ledgebrook | Valuation | The Stephens Group | |
| Sep, 2024 | Amount | Series B - Ledgebrook | Valuation | The Stephens Group , Brand Foundry |
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| Mar, 2024 | Amount | Series A - Ledgebrook | Valuation |
investors |
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| Date | Amount | Transaction Name | Valuation | Lead Investors | Investors |
|---|---|---|---|---|---|
| Jul, 2021 | Amount | Post-IPO - Grab | Valuation |
investors |
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| Feb, 2021 | Amount | Post-IPO - Grab | Valuation |
investors |
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| Jan, 2021 | Amount | Post-IPO - Grab | Valuation |
investors |
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| Feb, 2021 | Amount | Post-IPO - Grab | Valuation |
investors |
Investors in Ledgebrook
Ledgebrook has secured backing from 7 investors, including venture fund and institutional investors. Prominent investors backing the company include Floating Point, The Stephens Group and Brand Foundry. This diverse investor base provides strategic capital, industry expertise, and valuable network connections that support the company's growth initiatives, market expansion, and long-term value creation.
| Investor | Description | Founded Year | Domain | Location |
|---|---|---|---|---|
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Private equity firm focused on multiple sectors
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Founded Year | Domain | Location | |
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Venture capital fund investing in early-stage tech startups
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Founded Year | Domain | Location | |
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Corporate-backed venture capital firm focused on fintech, Insurtech, and multiple sectors
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Founded Year | Domain | Location |
| Investor | Description | Founded Year | Domain | Location |
|---|---|---|---|---|
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Single family office of Amitabh Bachchan, founder of Amitabh Bachchan Corporation or AB CORP
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Founded Year | Domain | Location | |
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Startup ecosystems are ignited through strategic investments by Signite Partners.
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Founded Year | Domain | Location | |
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Venture capital is directed toward companies in multiple sectors.
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Founded Year | Domain | Location | |
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Venture capital is invested in cybersecurity, fintech, and AI startups.
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Founded Year | Domain | Location |
Investments & Acquisitions by Ledgebrook
| Company Name | Description | Domain | Location | Founded Year | Amount |
|---|---|---|---|---|---|
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Bionic investment advisor platform
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2016 | ||||
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Fine Asian gourmet food is offered by an internet-first restaurant.
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2016 | ||||
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Physical e-commerce kiosks are deployed for rural purchases in Indonesia.
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2014 | ||||
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Fine Asian gourmet food is offered by an internet-first restaurant.
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2016 |
Financial Statements - Ledgebrook
| Date | Amount | Transaction Name | Valuation | Lead Investors | Investors |
|---|---|---|---|---|---|
| Jul, 2021 | Amount | Post-IPO - Grab | Valuation |
investors |
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| Feb, 2021 | Amount | Post-IPO - Grab | Valuation |
investors |
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| Jan, 2021 | Amount | Post-IPO - Grab | Valuation |
investors |
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| Feb, 2021 | Amount | Post-IPO - Grab | Valuation |
investors |
Ledgebrook Comparisons
Competitors of Ledgebrook
Ledgebrook operates in a dynamic and competitive business environment, facing competition from various established players and emerging companies in the market. The competitive landscape includes prominent companies such as Joyn Insurance, Optio Group, Insurance Quantified, elseco and BondCenter, among others. This competitive environment drives innovation, market differentiation, and strategic positioning as companies strive to capture market share and deliver value to their customers. Understanding the competitive dynamics is crucial for assessing market positioning, identifying growth opportunities, and navigating the challenges inherent in a competitive marketplace.
| Company Name | Domain | Founded year | HQ Location | Description |
|---|---|---|---|---|
| domain | founded_year | HQ Location |
Provider of insurance underwriting services
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| domain | founded_year | HQ Location |
Claims consulting and insurance underwriting services are provided.
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| domain | founded_year | HQ Location |
Offers AI-powered data ingestion and analytics for property and casualty underwriting.
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| domain | founded_year | HQ Location |
Insurance underwriting services are provided in Dubai.
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| domain | founded_year | HQ Location |
Offers an automated bonding solution tailored for insurance agents.
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| Company Name | Domain | Founded year | HQ Location | Description |
|---|---|---|---|---|
| domain | founded_year | HQ Location |
Multiple services are booked via an app-based platform.
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| domain | founded_year | HQ Location |
On-demand services are booked through an app-based platform.
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| domain | founded_year | HQ Location |
App based platform offering on demand delivery and ride-hailing services
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| domain | founded_year | HQ Location |
Operates an on-demand hyperlocal delivery app for food and groceries.
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Latest news on Ledgebrook
Frequently Asked Questions about Ledgebrook
When was Ledgebrook founded?
Ledgebrook was founded in 2021 and raised its 1st funding round 1 year after it was founded.
Where is Ledgebrook located?
Ledgebrook is headquartered in Boston, United States. It is registered at Boston, Massachusetts, United States.
Who is the current CEO of Ledgebrook?
Gage Caligaris is the current CEO of Ledgebrook. They have also founded this company.
Is Ledgebrook a funded company?
Ledgebrook is a funded company, having raised a total of $114.8M across 5 funding rounds to date. The company's 1st funding round was a Series A of $24M, raised on Apr 25, 2022.
What does Ledgebrook do?
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.
Who are the top competitors of Ledgebrook?
Ledgebrook's top competitors include Joyn Insurance, Qubit and Optio Group.
Who are Ledgebrook's investors?
Ledgebrook has 7 investors. Key investors include Floating Point, The Stephens Group, Brand Foundry, American Family Ventures, and Duquesne Family Office.