Gage Caligaris is the Founder and Chief Executive Officer of Ledgebrook, a tech-enabled E&S MGA looking to provide the fastest, easiest quoting experience to wholesale brokers while delivering best-in-class pricing and risk selection via a next-gen tech stack.
Prior to entering the world of insurance, Gage used his degree in Applied Mathematics from Harvard to trade exotic commodity derivatives at Barclays. His insurance career started in the Actuarial program at Liberty Mutual where he became the fastest person ever to pass the Casualty Actuarial exams. From there, various management positions culminated in the role of Senior Director of New Mobility Products where he spearheaded growth from <$50M to >$450M in GWP. His unique combination of entrepreneurial drive & deep insurance industry expertise represent the foundational bedrock of Ledgebrook. Gage lives in the Greater Boston area with his wife and two children.
I have always been a math guy. After college I worked for a bit on Wall Street trading exotic derivatives, but then I took a hard left into insurance - mainly for family reasons. My wife and I wanted to settle near her parents in Massachusetts. I found out that Liberty Mutual runs the largest actuarial program in the country, if not the world, just down the road from the in-laws. So, I figured I would take a bunch of math exams, become an insurance executive, start our family and in time having really learnt a trade deeply - I would find my own thing. Living the dream!
I became the fastest person ever to pass the actuarial exams at Liberty and rose through the business over a decade, running pricing teams - including for some of the product areas we do now at Ledgebrook - and growing a mobility business from ~$40 million to ~$500 million the last 2 years I was there. By 2022 I felt ready to hang my own shingle. I had a vision of bringing together the best of modern technology and the best of insurance expertise when most competitors seemed to be heavily tilted towards one or the other. I saw that it had massive commercial potential but was just not possible to do in a large incumbent carrier. I remember, for example, at one point I was quoted 7 years(!) to implement a technology change that I knew could be done in less than 10% of the time by true Silicon Valley tech talent.
Really all I want to do over the next 40 years is build the best possible insurance company at scale, with the best people and tech and spend whatever free time I have raising my family. There will be no second act for me, I plan to die in the chair. It's that simple.
The Excess and Surplus lines market is enormous. Over $100 billion in the US and growing as more and more business gets moved from the tightly-regulated - "admitted" - market. It's competitive but inefficient as a consequence of all the incumbent players being encumbered by technology debt, out of date data and massive cultural barriers to change. You see inefficient levels of service, and inefficient pricing because people are steering that pricing while looking in the rearview mirror. This situation persists because of the barriers to market entry. Ledgebrook has crashed through those barriers to entry powered by our mission to delight the wholesale brokers (our customer). With our tech and culture we are able to provide a level of service they haven't seen before. And we can manage our business and manage our pricing in real time in a way the capacity providers haven't seen before either. It's a winning formula.
"With our tech and culture we are able to provide a level of service they haven't seen before. And we can manage our business and manage our pricing in real time in a way the capacity providers haven't seen before either. It's a winning formula."
We started off with General Liability which remains our flagship product. We then launched Professional Liability and have just launched an Unsupported Excess offering. During 2025, we plan to launch a further three products - stay tuned. While there are lots of formidable barriers to entry in insurance markets, they are also markets based on relationships where people talk. It was really hard at the beginning for sure. People were like "who are you? Will you be around in two years?" and we needed to lean hard into the team's pre-existing personal relationships in wholesale brokers and capacity providers. But now our reputation for Ledgebrook speed and expertise goes before us and we have been blown away by the response. I see it everyday in the stats on submission growth from our broker partners, who just love what we are doing.
The Colonel never fully gives away his recipe right!? But what I can say is we have a fantastic 20-strong technology team led by our CTO Nathan Hall who are fully embedded with our underwriting staff at both the leadership and desk level. They have built and continue to build amazing things.
Our speed and pricing is underpinned by our use of cutting-edge proprietary tech - get the submission cleared & rated with 3rd party data and on the underwriter's desk as fast as possible so we can be the first quote back to the broker.
It's also about culture. It's no good having the tech if the underwriter doesn't trust or embrace it. Or if the tech processes the submission superfast but it sits in the underwriter's inbox for hours or days at a time that's no good either. You really need to have the "best of both worlds" - I like to talk about our tech being an F1 car, team Ledgebrook being the driver, and our culture being the fuel.
"Our speed and pricing is underpinned by our use of cutting-edge proprietary tech - get the submission cleared & rated with 3rd party data and on the underwriter's desk as fast as possible so we can be the first quote back to the broker."
There's indeed a lot of noise about these technologies! But the signal - and my lived-experience - is that with great engineering and implementation there are direct use cases that hit the expense ratio and loss ratio for insurers in a big way. We use Al to streamline a number of "micro tasks" that take up significant underwriter time but are basically just googling stuff about the account.
For example, what is the correct NAICS classification or what time does this bar/restaurant really close (somehow all the applications say midnight but all the claims happen at 2 am). On a more global level we are also using proprietary Al bots to answer questions about the hundreds of pages of underwriting guidelines - more than any individual underwriter can possibly digest with 100% accuracy and sifting through the docs for that one relevant paragraph can be like searching for a needle in a haystack. The Al allows us to support underwriters in getting to the right answer on how to apply them much more efficiently than would otherwise be the case.
This is a constant theme for me as the CEO. I have to balance the need to invest in our underwriting teams, operations, and new product launches with investment in our tech and longer-term R&D. There's often more of a direct line of sight to top line growth from the former, but we all know in the senior leadership team that our tech is a big part of what differentiates us and will continue to give us our sustainable edge as we scale. Thankfully, I have a great leadership team, and supportive board, where we can talk about these trade-offs openly and find our way through.
"We all know in the senior leadership team that our tech is a big part of what differentiates us and will continue to give us our sustainable edge as we scale."
We are really excited to partner with MS Transverse alongside Obsidian who support our PL program. The transition to MS Transverse gives us A-rated paper which basically means that our teams can offer our distribution partners and the end insureds a more secure product as its written on a larger, more stable balance sheet. The transition has also expanded our underwriting "box" so we can respond more flexibly to opportunities we are already seeing but for which we couldn't offer market competitive product in the past. MST is also excited to support future Ledgebrook product launches. As the top brand in the fronting carrier marketplace, MST choosing to work with us provides further validation for Ledgebrook in the eyes of our broker and reinsurance partners.
We have had some wonderful backing so far. From Brian Spaly of Brand Foundry at the beginning, to Mike Mansell of American Family Ventures leading the A- round and the Stephens Group & Duquesne Family offices more recently.
I think what all these partners have in common is excitement about the vision of bringing together the best of insurance expertise and technology; understanding that the market is huge and there are examples of very valuable businesses with relatively small established market shares; and a commitment to backing a business being built for the long haul. It helps too that they see us doing what we say we will and communicating openly with them as true partners.
Well, let's put it this way. We wrote our first policy in May 2023, and we have just passed a $100 million run rate of premium and are only scratching the surface of all the thousands of submissions we already get from wholesale partners every month. We are ahead of schedule if you look at our progress and momentum compared both to successful InsurTechs and Specialty insurance start ups of the recent past.
From my very first investor meetings I would tell people that the long-term vision was to bring the best of technology to bear on building the digitally enabled, next generation version of a Berkshire Hathaway or Munich Re. To be honest some people laughed it off.
But I was always clear and confident in my own mind that the addressable markets for this offering are huge, and it is basically impossible for anyone to do it unless you can build it ground up with true insurance expertise. You need to break through the formidable barriers to entry and have a really long-term vision. It's still early innings for Ledgebrook, but I am so proud of what we have accomplished so far as a team, and I am fully confident we are positioned to build a truly great insurance business at scale over the long term.
You need to be excited to be part of building something, and to do things differently in our industry. You need to be willing to work hard and to wear many hats. If that's you, come talk to us at Ledgebrook for sure as you explore your next step. We have so much fun as a team every day and we are just getting started.
"It's still early innings for Ledgebrook, but I am so proud of what we have accomplished so far as a team, and I am fully confident we are positioned to build a truly great insurance business at scale over the long term."
