Ledgebrook Valuation, Funding & Investors
Ledgebrook is valued at $60M as of April 2023.
Last Ledgebrook valuation
$60M
Seed · Apr 2023
Last Ledgebrook funding round
$65M
Series C · Jun 2025
Cumulative funding Ledgebrook raised
$115M
across 5 funding rounds
Key investors in Ledgebrook
Brand Foundry Ventures
American Family Ventures
Floating Point
Stephens Group
Duquesne
Hummingbird Ventures
About Ledgebrook
Ledgebrook is a technology-enabled managing general agent in the excess and surplus insurance market. Targeting wholesale brokers, it delivers rapid quoting via a modern tech stack for property, casualty, and specialty lines. Led by industry veterans and headquartered in New York, the firm aims for global reinsurance scale with superior risk selection and pricing algorithms.
Founded
2022
HQ
Boston, MAWebsite
Status
Privately held
Customer focus
B2B
Revenue model
Product sales
Valuation
$60M (Apr 2023)
Ledgebrook Valuation
Ledgebrook is currently valued at $60M, based on its seed round in April 2023.
The $5M round was led by Markd, with participation from Brand Foundry Ventures.
Ledgebrook's valuation has grown 3.0x from $20M at its seed round in June 2022 to $60M in April 2023, across 2 priced rounds.
Ledgebrook valuation by funding round
| Date | Stage | Valuation |
|---|---|---|
| Apr 2023 | Seed | $60M |
| Jun 2022 | Seed | $20M |
Ledgebrook Funding History
Ledgebrook has raised a total of $115M across 5 funding rounds.
Ledgebrook's first fundraising round was a $4M seed round in June 2022. The most recent completed round was a $65M Series C in June 2025.
Ledgebrook funding rounds
| Date | Stage | Investors | Raised | Valuation | Deal Summary |
|---|---|---|---|---|---|
| Jun 2025 | Series C | Stephens Group (lead); Brand Foundry Ventures; American Family Ventures; Hummingbird Ventures; Floating Point; Duquesne | $65M | - | Ledgebrook Inc. is a US-based insurtech specializing in excess and surplus (E&S) lines insurance, operating as a technology-driven managing general agency (MGA) that offers general and professional liability products through a platform focused on wholesale brokers. The company combines insurance expertise with technology to deliver client-service-led solutions, enabling new product offerings and risk retention on behalf of carrier partners. On June 20-25, 2025, Ledgebrook closed an oversubscribed $65 million Series C funding round led by existing investor The Stephens Group, with participation from existing backers Duquesne, Brand Foundry Ventures, Floating Point, and American Family Ventures, plus new investor Hummingbird Nomads (also referred to as Hummingbird Ventures). This brings total funding to over $110 million, following a $17 million Series B in September 2024 and a $24 million Series A in March 2024 led by American Family Ventures. Ryan Morrow, managing director at Stephens Group, joined Ledgebrook’s board, while management and employees remain the largest shareholders. Proceeds will support team expansion, enhancement of client services for wholesale brokers, introduction of new insurance products, and increased risk retention participation. CEO Gage Caligaris highlighted the round's recognition of business momentum and alignment with investors' long-term partnership approach. Stephens Group praised Ledgebrook's founder-led execution in the attractive E&S market. Ledgebrook positions itself as a premier E&S platform emphasizing consistent execution, broker delight, and tech-insurance integration. Leadership includes President John Mullen, with prior experience at Liberty Mutual. Stephens Group manages over $2 billion in private equity, focusing on high-growth companies in sectors like vertical software. |
| Sep 2024 | Series B | Duquesne (lead); Brand Foundry Ventures; American Family Ventures; Stephens Group | $17M | - | Ledgebrook is a Boston-based insurtech managing general agent (MGA) founded in 2022, specializing in the Excess and Surplus (E&S) insurance market. The company provides a tech-enabled platform that delivers the fastest quoting experience to wholesale brokers, best-in-class pricing, and risk selection through a next-gen tech stack, with ambitions to become a globally diversified re/insurer. On September 12, 2024, Ledgebrook closed a $17 million Series B funding round led by Duquesne Family Office, with participation from The Stephens Group, Brand Foundry Ventures, and American Family Ventures. This opportunistic raise follows a $24 million Series A announced in March 2024 and will fund acceleration of current operations expansion and new innovative projects. The round coincides with the appointment of Anthony Segal-Knowles as CFO, bringing expertise from Lazard, the British Treasury, and the International Monetary Fund. Ledgebrook's leadership, including Founder and CEO Gage Caligaris, emphasized the alignment of new investors' long-term thinking with the company's vision. Investors highlighted the need for better technology in the E&S market for placing difficult risks. In June 2024, the company expanded its professional lines with a new architects and engineers insurance product in partnership with Obsidian Insurance. |
| Mar 2024 | Series A | American Family Ventures (lead); Brand Foundry Ventures; Floating Point | $24M | - | Ledgebrook is a technology-driven excess and surplus (E&S) lines insurtech and managing general agent (MGA) founded around 2021-2022, focusing on redefining the insurance experience for wholesale brokers through cutting-edge technology, particularly in placing difficult risks in the Excess and Surplus market, including professional lines like architects and engineers insurance in partnership with Obsidian Insurance. The company operates fully remotely in the US, emphasizing team equity packages and client-service-led approaches. On approximately March 28, 2024 (noted as March or April 28 in sources), Ledgebrook announced a $24M Series A funding round led by American Family Ventures, with participation from Brand Foundry Ventures and Floating Point, as confirmed across multiple reports including Stephens Group press release and Life Insurance International. This followed earlier rounds like seed ($4.2M-$4.6M in 2022-2023) and preceded a $17M Series B on September 11-12, 2024 led by Duquesne Family Office with Stephens Group, American Family Ventures, and Brand Foundry Ventures, then a $65M oversubscribed Series C in June-July 2025 led by Stephens Group with prior investors plus Hummingbird Nomads. Total funding reached ~$110.6M across 4-5 rounds by mid-2025. The funds from the Series A and subsequent rounds supported operational expansion, new product launches, talent acquisition, risk retention, and innovative projects, with addition of CFO Anthony Segal-Knowles around Series B. Ledgebrook has shown rapid growth, raising opportunistically post-Series A, attracting family offices and VCs like Duquesne and Stephens Group for their long-term alignment, positioning it as a premier E&S platform amid investor confidence in founder Gage Caligaris's vision to build a leading insurance technology platform for brokers. |
| Apr 2023 | Seed | Markd (lead); Brand Foundry Ventures | $5M | $60M | Ledgebrook is a Boston-based insurtech managing general agent (MGA) founded in 2022, focusing on middle-market excess and surplus (E&S) lines, providing fast quoting experiences for wholesale brokers via a tech-enabled platform combining underwriting expertise and modern technology. On April 25, 2023, Ledgebrook closed a $4.6 million funding round structured as an uncapped SAFE, led by Markd with participation from Brand Foundry Ventures and other angels, bringing total funding raised to $8.8 million following a prior $4.2 million seed round. The round valued the company at a $60.29 million post-money valuation with a $7.24 price per share. Funds were allocated to scale the flagship non-admitted general liability and supported excess liability products, develop future offerings, staff up, and enhance technology and operations. Ledgebrook launched its first product amid positive reception and partnered with Everspan Group earlier in 2023 for mid-market general liability and excess liability programs. Parker Beauchamp from Markd joined the team, bringing experience from placing over $1 billion in premiums. |
| Jun 2022 | Seed | Brand Foundry Ventures (lead); American Family Ventures | $4M | $20M | Ledgebrook is a Boston-based insurtech managing general agent (MGA) founded in March 2022, focusing on the Excess and Surplus (E&S) market for wholesale brokers. It offers technology-driven solutions like a broad-appetite E&S general liability (GL) product with supported excess, aiming to improve automation, pricing, and outdated platforms in the sector. In 2022, Ledgebrook raised $4.2 million in a seed funding round led by Brand Foundry Ventures, with participation from American Family Ventures and 15 angel investors. The funds supported expansion of operations, launch of disruptive products, implementation of new technologies for E&S markets, and writing its first policies in Q4 2022. The leadership team, including founder and CEO Gage Caligaris (an actuary), brings industry veteran expertise to enhance rates for insureds and serve underserved segments with slow tech adoption. Subsequent rounds included a $4.6M raise in April 2023, $24M Series A in March 2024 led by American Family Ventures, $17M Series B in 2024 led by Duquesne Family Office, and $65M Series C in June 2025 led by The Stephens Group. |
Who has invested in Ledgebrook?
7 investors have backed Ledgebrook across its funding rounds, including Brand Foundry Ventures, American Family Ventures, Floating Point, Stephens Group, Duquesne and Hummingbird Ventures.
Lead investors include Stephens Group, Duquesne, American Family Ventures, Markd and Brand Foundry Ventures.
Ledgebrook Investors
| Investor | HQ | Rounds | Role | First check |
|---|---|---|---|---|
| Austin, TX | 5 | Lead | Jun 2022 | |
| Madison, WI | 4 | Lead | Jun 2022 | |
| United States | 2 | Participant | Mar 2024 | |
| Pittsburgh, PA | 2 | Lead | Sep 2024 | |
| Little Rock, AR | 2 | Lead | Sep 2024 | |
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Benchmark 350K+ Funding Rounds and Disclosed VC Valuation Multiples
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Start Free TrialLedgebrook Competitors
Ledgebrook competitors include listed companies like Niyogin Fintech and Veefin, and private ones like PAXAFE, Ergos, Grand Guardian Life Insurance Company and Growth Street.
| Company | HQ | Status | Revenue | EBITDA | Valuation |
|---|---|---|---|---|---|
| Indianapolis, IN | Private | - | - | $42M | |
 Samastipur | Private | - | - | $60M | |
 Yangon | Private | - | - | $60M | |
 London | Private | - | - | $60M | |
| India | Publicly listed | $25M | $1M | $63M | |
| India | Publicly listed | $36M | $8M | $64M |
Ledgebrook Public Comps
Ledgebrook is still privately-owned, but its public comps include Niyogin Fintech, Veefin, Minupar Participacoes, Kruso Kapital, RMS Mezzanine, Purple Finance, Time Finance, Sygnus Credit Investments, ALBIS Leasing and Delfin.
| Last FY | EV/Revenue | EV/EBITDA | ||||||
|---|---|---|---|---|---|---|---|---|
| Revenue | EBITDA | Last FY | LTM | 2027E | Last FY | LTM | 2027E | |
| $25M | $1M | 2.8x | - | 52.5x | - | |||
| $36M | $8M | 2.4x | - | 10.5x | - | |||
| $85M | $81M | 0.4x | - | 0.4x | - | |||
| $43M | - | 4.6x | - | - | - | |||
| $3M | - | 71.4x | - | - | - | |||
| $3M | ($729K) | 17.2x | - | (81.2x) | - | |||
| $50M | $11M | 1.4x | 1.3x | 6.0x | 5.4x | |||
| - | - | - | - | - | - | |||
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Common questions about Ledgebrook
| When was Ledgebrook founded? | Ledgebrook was founded in 2022. |
| Where is Ledgebrook headquartered? | Ledgebrook is headquartered in Boston, MA, United States. |
| Is Ledgebrook publicly listed? | No, Ledgebrook is a private, VC-backed company. |
| What is Ledgebrook's valuation? | Ledgebrook was last valued at $60M in its seed round in April 2023. |
| How much funding has Ledgebrook raised? | Ledgebrook has raised $115M across 5 funding rounds. |
| What was Ledgebrook's last funding round? | Ledgebrook's last funding round was a $65M Series C in June 2025, led by Stephens Group. |
| Who are Ledgebrook's investors? | Ledgebrook's investors include Brand Foundry Ventures, American Family Ventures, Floating Point, Duquesne, Stephens Group, Hummingbird Ventures and Markd. |
| Which companies are comparable to Ledgebrook? | Companies comparable to Ledgebrook include PAXAFE, Ergos, Grand Guardian Life Insurance Company, Growth Street, Niyogin Fintech and Veefin. |
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