There’s something quietly savage about building a $766 million company in an industry most of tech still side-eyes like it’s wearing a flip phone and a Members Only jacket. Ledgebrook didn’t show up to be cute, they showed up to dominate. And if you’re not watching what Gage Caligaris and his crew are doing in E&S, you’re asleep at the terminal.
Less than three years ago, Caligaris walked out of Liberty Mutual after turning a niche portfolio into $450M+ in Gross Written Premiums and became that guy who bet his actuarial mind and Harvard math brain on wholesalers, the most overlooked rainmakers in commercial insurance. No AI smoke and mirrors, no stealth-mode mystique, just speed, service, and underwriters who still believe in showing up to shake hands. Revolutionary, right?
Fast forward to June 2025. Ledgebrook just locked in a $65 million Series C, led by returning heavyweight The Stephens Group. They doubled down on what they already knew, this isn’t a bet, this is an inevitability. Ryan Morrow, Managing Director at The Stephens Group, now has a seat on the board to help steer the rocketship. The table’s also stacked with Duquesne Family Office, Brand Foundry Ventures, Floating Point, American Family Ventures, and new entrant Hummingbird Nomads. That cap table isn’t just well-funded, it’s well-read.
From May 2023 to December 2024, the company went from writing its first policy to breaking a $100 million annual run rate. That’s not growth, that’s velocity. From 30 to over 100 employees, all fully remote, serving 50 states plus DC, across sectors like construction, real estate, hospitality, and retail. And they’re doing it with a Socotra-powered platform implemented in four months flat. The quoting engine isn’t just fast, it’s the fastest. Think instant eligibility, prefilled data, and risk selection that makes your average submission feel prehistoric.
Under the hood? They swapped out shiny AI toys for hard-nosed operational execution. While others chase headlines, they build trenches. Their general and excess casualty lines just moved from Everspan to MS Transverse, lifting coverage thresholds and widening appetite for complex risks. And with new product drops every six months, including A&E insurance in partnership with Obsidian Insurance, they’re playing the long game like it’s already theirs.
Shoutout to Nathan Hall, Adrian Copland, Anthony Segal-Knowles, John Mullen, Christopher Grether, and VP leads Nicole Kessler, James Lassiter, and Scott Carr. This squad isn’t here to talk disruption, they’re here to price it, underwrite it, and bind it before lunch.
