Gage Caligaris said that during his first date in his last month at Harvard University, he decided to marry his current wife. A few years later, he made another important decision: to leave Wall Street and start over as an insurance intern in order to be closer to his wife's family in Boston.
This mathematics graduate was trading complex derivatives in New York at the time, and he described that period of his career as "fast-paced and also very interesting." (His LinkedIn profile shows that he held three positions as a trader, one of which was at Barclays Capital in New York.) Caligaris, from Yardley in Pennsylvania, recalls that he was in a long-distance relationship for a year, commuting between New York and Boston by Chinatown bus until his future wife moved down to be with him.
“I’ve taken the Chinatown bus so many times,” he said to Fortune. He still supports the Philadelphia Eagles to this day.
But his wife's parents lived in Boston, and after working on Wall Street for about three years, he wanted to find a path north. He was originally considering attending business school, but later his sister, who had interned in an actuarial program at Travelers, introduced him to a profession that he said he had never heard of before.
“She told me that it was just a bunch of math exams. If everything goes well, you can become a senior executive in the insurance industry,” said Caligaris, who studied applied mathematics at the undergraduate level. “So, with these two sentences in mind, I did a quick search on Google.”
That search led him to Liberty Mutual. He joined there in 2014 as an intern. Today, this 38-year-old entrepreneur is in charge of Ledgebrook, a specialty insurance platform based in Boston that is native to AI. He has just completed a round of financing of $200 million, co-led by Allianz X and Rockefeller Capital Management. According to a person close to the company, this transaction has raised the company's post-funding valuation to $2.6 billion, bringing it into the unicorn category for the first time.
The same principle applies to calculations related to family matters as well.
“My father-in-law and mother-in-law still help us take care of the children every weekend,” says Caligaris, who is now a father to three children. “So that part is going quite smoothly as well.”
In the cafeteria
Ledgebrook was established in 2022 to provide insurance for medium-sized enterprises that face complex or difficult-to-underwrite risks. The company sells its products exclusively through wholesale brokers, offering coverage such as general liability insurance and professional liability insurance. Its technology assists underwriters in assessing these risks and determining the premium rates. The company claims that it can typically provide quotes within a few hours, rather than on a weekly basis.
It operates in what is known within the industry as the Excess and Surplus (E&S) market, which encompasses all the risks that standard insurance companies are unwilling to underwrite. Caligaris estimated the premium volume of this market at $143 billion last year, with an annual growth rate of about 10%. He stated that the average policy value in this market “far exceeds” $100,000, with some policies even reaching several million dollars.
Many startups are promoting insurance products driven by AI. Caligaris believes that in his niche market – large-value policies underwritten through wholesale brokers – there “are actually no technical competitors.” He explains that the reason is that reinsurance companies are very cautious about to whom they entrust such tasks.
In his view, the social logic of this industry boils down to trust. He describes the decisions made by reinsurance companies as essentially saying, “Hey, Gage, write out $250 million on my behalf, and I’ll accept the outcome.” Even after multiple reviews, the need for trust in the people who make those decisions cannot be eliminated.
"Reputation is very important," he said. "And it has a two-way effect, with both benefits and drawbacks."
To win this kind of trust also means having to navigate within the social order of the industry.
“The insurance industry is a bit like a high school cafeteria,” said Caligaris. If established companies feel that a newcomer is taking away their business, they might start telling others not to cooperate with that company, or imply that it is cutting corners. Until now, Ledgebrook has always been keen to avoid such conflicts.
"We've always tried our best to stay close to the core circle, operate in a low-profile manner, and focus on execution," he said. Although this round of financing is the D-round for Ledgebrook, the company had not previously disclosed any early-stage financings, even though its underwriting premiums have approached $1 billion.
"Writing down so much premium without everyone paying much attention indicates that you have actually been making steady progress in the industry," he said.
This caution also reflects Ledgebrook's early dependence on other companies. The company initially operated with a structure that managed general agents ( MGA ). Caligaris described this model as: it looked like, sounded like, and operated like an insurance company, but in reality, it relied on others' licenses and external reinsurance to issue policies.
"We've done 95% of the work, but the funds are elsewhere," he said.
Ledgebrook now has its own insurance underwriting entity, which received an A-financial strength rating awarded by AM Best in August 2026. Caligaris says that this makes the company more independent in its operations. He expects that Ledgebrook will accumulate underwriting premiums of over $1 billion within four to six weeks.
Allianz's American bets
Caligaris said that Allianz spent three months reviewing this business before making the investment. He mentioned that Allianz X participated in this round of $200 million equity financing, while Allianz Re separately agreed to provide a multi-year reinsurance underwriting capacity arrangement.
Allianz X indicates that this investment fills a gap in its property and accident insurance platform in the United States, increasing exposure to medium-sized general liability risks in the E&S market. Its CEO, Nazim Cetin, described this investment in a statement as a counter-bet on the industry's AI application direction.
"The industry is first applying AI to the simplest risks, as those are the areas where automation is easiest to implement," says Cetin. "We believe that greater opportunities lie on the other end, in the complex and underwriting-challenged businesses, where underwriting judgment is scarce and the cost of slow decision-making is the highest."
It's not just this type of investor who is betting on Ledgebrook. Caligaris mentioned that the company has also received approaches from private equity firms and hedge funds, which are interested in providing reinsurance in a secured manner, as such returns are unrelated to market trends.
“No matter which way the wind blows, it has nothing to do with the stock market,” he said. “I think you’ll see more and more funds flowing towards forward-thinking players like us.”
This collaboration also brought Caligaris to Munich, where Allianz hosted him for the Oktoberfest last week.
“There are some rather embarrassing photos of me wearing leather pants circulating outside right now,” he said.
Less paperwork, more hockey.
The selling point of Ledgebrook is that it allows the software to handle the preliminary preparations, freeing experienced insurance professionals to make judgments and focus their time on brokers who can generate business.
Its proprietary platform Blackbird reads the documents submitted in the insurance application, classifies the risks, and calculates the technical fees. Experienced underwriters make the final decision. Caligaris says that instead of spending time collecting information and preparing documents, it is better to make phone calls, discuss terms, or meet with brokers in person.
"Our people spend their time watching hockey games with brokers," he said. "Or having steak dinners."
When brokers ask if it is possible to reduce prices by increasing the deductible or adjusting the coverage, these relationships are still very important. The role of technology is to make it easier for underwriters to respond, rather than to eliminate this type of communication.
“If you ask our brokers what we’re doing, they’ll say we’re answering calls,” said Caligaris.
In some cases, companies also hand over the tools directly to their partners. Caligaris mentioned a user who runs a real estate investment company that buys and sells commercial properties. The property insurance could be arranged quickly, but the liability insurance would take several weeks to process, and during that waiting period, the transactions kept falling through. Ledgebrook provided him with a robot that could connect in real-time to the company’s system to get quotes, which were about 25% higher than the usual company charges. Caligaris said that this user was aware of this, but still used it because getting a quote now was much better than waiting three weeks for a cheaper one—by then, someone else might have already taken the property.
Some of the improvements he described may not be as futuristic as they sound with the AI tag. Recalling the early days of his entrepreneurship when interviewing underwriters, he remembers that a candidate asked him how many more years it would take to be able to generate an insurance policy with just one click, like with PDF.
“Guys, this feature has been available for a long time already,” he remembers answering like that at the time. The candidate told him that they had heard similar promises before, yet several years later, they were still dealing with handwritten insurance policies.
He also recalled that one Saturday morning last summer, upon waking up, he received an email from the person in charge of the RT Specialty distribution business. Around 4:30 p.m. the previous day, a major client in San Diego lost a layer of umbrella-style insurance coverage on a policy and called Ledgebrook for assistance. Caligaris said that his team quickly provided an alternative quote and completed the underwriting before 4:45 p.m.
“Everyone orders dinner,” he said. The next morning, an email of gratitude arrived.
The company claims to have around 300 employees, including approximately 80 underwriters and 50 engineers. Caligaris mentioned that the company's underwriting performance has always been good, however, he did not provide any data on the loss ratio during the interview.
A slide and a smile
Insurance was not the destination he had originally anticipated, but entrepreneurship has always been part of the plan. During his time at Liberty Mutual, he was in charge of managing the pricing team and claimed to have built a $500 million travel insurance business, with clients including Uber, Lyft, Turo, and Waymo. This experience provided him with the knowledge and skills needed to launch products onto the market and establish cooperative relationships before founding Ledgebrook.
After reading "From 0 to 1," he began to realize the possibilities of his career path. He remembers thinking to himself at that time, "Oh my god, I am a tech founder." When he decided to start his own business, he said his first task was to create a 30-slide presentation about the culture of the company he hoped to work for the rest of his life.
This led to an unusual compensation model: a base salary and Ledgebrook equity, but no bonuses, target premiums, or performance evaluations, said Caligaris. He believes that annual targets would encourage underwriters to take on more business or lower prices at the end of the year in order to meet their quotas. In the last few weeks of December, he said, “Everyone starts to scrutinize every policy carefully.”
“If you write $4.9 million, you’re the villain; if you write $5.1 million, you’re the hero,” he said. “Is it really that important?”
This round of financing is a milestone for the founder who claims to have started with "a slide and a smile," but he says he hopes to avoid a "show of success" and instead focus on building a company that can weather the cycles of the insurance market.
For this founder who changed careers in order to be closer to his family, the current plan is to stay put.
“I will sit in this chair until I die,” he said. “I will take care of household affairs, I will work on Ledgebrook, and I will build the insurance company that I once wanted to join and grow within.”
This research was assisted by and/or transcribed using the generative AI. Reporters independently reported and verified the factual statements in the text, which were also reviewed by human editors before publication. The report has been updated to clarify the scope of investments made by Allianz.
