Ledgebrook is a technology company.
Ledgebrook has raised $74.0M across 3 funding rounds.
Ledgebrook has raised $74.0M in total across 3 funding rounds.
Ledgebrook has raised $74.0M in total across 3 funding rounds.
Ledgebrook's investors include American Family Ventures, Markd VC.
Ledgebrook Insurance, LLC is a tech-enabled Excess & Surplus (E&S) Managing General Agent (MGA) founded in 2021 and headquartered in Boston, MA. It specializes in specialty insurance products like general liability, professional liability, and excess liability, targeting wholesale brokers with the fastest quoting experiences, best-in-class pricing, and superior risk selection powered by a next-generation tech stack.[1][2][3] Serving the insurance industry burdened by legacy systems, Ledgebrook solves inefficiencies in quoting and underwriting through streamlined, internal-facing technology that enriches submissions, prefills data, and enables real-time analytics—without requiring brokers to change workflows.[1][3][5] The company has shown strong growth momentum, raising $24 million in Series A and $17 million in Series B funding, employing 85 staff (including 20 in-house programmers), managing significant gross written premiums, and recently transitioning casualty and excess products to MS Transverse paper while expanding leadership.[2][3]
Ledgebrook was founded in 2021 by Gage Caligaris, a Harvard Applied Mathematics graduate who transitioned from trading exotic commodity derivatives at Barclays to insurance, where he excelled as the fastest to pass Casualty Actuarial exams at Liberty Mutual and scaled New Mobility Products from under $50M to over $450M in gross written premiums (GWP).[1][4] Drawing on his entrepreneurial drive and deep industry expertise, Caligaris launched Ledgebrook to modernize specialty insurance, an sector lagging behind other industries due to outdated technology and processes.[1] Early traction came from its tech-driven focus on speed, with the company quickly launching successful products, building a leadership team of insurance veterans—like COO Adrian (ex-AXA XL innovator who 10x'd a road safety startup), actuary Ruiqi (ex-Liberty Mutual, Deloitte), and engineer Nathan (fintech background)—and achieving recognition as a highflier alongside peers like Coterie and Vouch.[2][4]
Ledgebrook rides the InsurTech wave transforming specialty E&S insurance, a $100B+ market slowed by legacy tech, by deploying modern stacks for digital-native efficiency amid rising demand for small/mid-sized multifamily and casualty coverage.[1][2][3] Timing is ideal post-2021 launch, capitalizing on post-pandemic market hardening, broker needs for speed in competitive quoting, and AI/ML adoption for underwriting—positioning it against incumbents while partnering with carriers like MS Transverse.[2][5] It influences the ecosystem by setting benchmarks for broker experiences (e.g., phone/email accessibility, flexible retentions), fueling highflier status, and inspiring full-stack re/insurer evolution, all while leveraging tools like Sensible for data extraction to cut manual entry.[2][3][5]
Ledgebrook's trajectory points to aggressive expansion: new product launches, enhanced AI/ML in its stack, global diversification as a full-stack re/insurer, and potential surprises amid $41M+ funding fueling hires and ops.[1][2] Trends like AI-driven underwriting, E&S market growth, and insurtech consolidation will propel it, evolving its influence from nimble MGA to global competitor challenging legacy carriers. This modernizes a vital industry, delivering the speed and expertise brokers crave—poised to redefine specialty insurance at scale.[1][3]
Ledgebrook has raised $74.0M across 3 funding rounds. Most recently, it raised $65.0M Series C in June 2025.
| Date | Round | Lead Investors | Other Investors |
|---|---|---|---|
| Jun 1, 2025 | $65.0M Series C | American Family Ventures, Markd VC | |
| Apr 1, 2023 | $5.0M Seed | Markd VC | |
| Jun 1, 2022 | $4.0M Seed | American Family Ventures, Markd VC |