Ledgebrook

How Gage Caligaris Built a $100M Run Rate InsurTech in 19 Months

March 14th, 2025

Founded By

Gage Caligaris

Monthly Revenue

$100M

Days To Build

425

Founders

Employees

100 (est.)

Profitable

Yes

Days To Build

425

Year Started

2022

Founded By
Gage Caligaris: Monthly Revenue
$100M: Days To Build
425

Founders
1: Employees
100 (est.): Profitable
Yes

Days To Build
425: Year Started
2022

Who is Gage Caligaris?

Gage Caligaris, the founder and CEO of Ledgebrook, holds an Applied Mathematics degree from Harvard and previously worked as a trader at Barclays before spending over eight years at Liberty Mutual, where he became the fastest to pass the Casualty Actuarial exams and led initiatives in new mobility products, driving significant growth in GWP.

What problem does Ledgebrook solve?

Ledgebrook addresses the frustration of wholesale insurance brokers who face slow and inconsistent service by offering a faster, more reliable, and seamless quoting process that combines advanced technology with deep industry expertise. This approach significantly reduces the wait times and unpredictability that brokers endure, allowing them to efficiently serve their clients and creating a compelling reason for them to choose Ledgebrook repeatedly.

How did Gage come up with the idea for Ledgebrook?

Gage Caligaris came up with the idea for Ledgebrook by combining his extensive actuarial experience with his passion for modern technology. Having spent over eight years at Liberty Mutual, he worked on new mobility products and was involved in creating innovative insurance solutions for emerging markets like autonomous vehicles and ride-sharing. This experience inspired him to think about how he could streamline insurance quoting processes by integrating advanced technology with deep industry expertise, using his unique blend of skills in applied mathematics and his experience from his previous roles at Barclays and Liberty Mutual.

Gage observed significant inefficiencies in the excess and surplus (E&S) insurance market, particularly with the slow and outdated technology used by established insurers. His firsthand experience managing new mobility products at Liberty Mutual revealed that even with substantial growth under existing constraints, larger insurers could not keep pace due to their significant legacy systems and cultural barriers.

Before launching Ledgebrook, Gage validated his idea by pinpointing the underutilized potential of the E&S market and recognizing a gap in leveraging modern technology. By focusing on speeding up the quoting process and enhancing service quality for wholesale brokers, he saw an opportunity to blend his actuarial expertise with cutting-edge tech solutions.

Gage faced early challenges, particularly with the numerous barriers to entry and skepticism from industry partners due to the limited track record of a new startup. He leveraged the experience he gained at Liberty Mutual, where he successfully grew a line of business significantly within a short period. This success gave him confidence to launch Ledgebrook and develop a more tech-driven approach to better serve wholesale brokers. By maintaining a strong focus on delivering fast and consistent quotes, Gage was confident that Ledgebrook could quickly gain traction in the large and growing E&S insurance market.

A key lesson Gage learned was the importance of blending industry expertise with modern technology. His deep actuarial background and love for building solutions drove him to explore technological strategies that could overcome inefficiencies he encountered in traditional insurance environments. Through open communication and collaboration between his engineering and underwriting teams, Gage refined the idea for Ledgebrook, ensuring their solutions were both innovative and workable in real-world scenarios. Despite initial challenges, Gage emphasized the importance of networking, relationship building, and demonstrating reliability to develop trust within the industry.

How did Gage Caligaris build the initial version of Ledgebrook?

Ledgebrook's initial product development journey centered around creating a fast and efficient quoting experience for the E&S (Excess and Surplus) market, leveraging advanced technology and deep industry expertise. The team employed a modern tech stack and integrated AI to streamline the intake and triage of insurance submissions, allowing these to be processed more efficiently. They utilized Secotra, a sophisticated policy administration system, which enabled quick product launches and adaptation to market demands. Building the necessary frameworks and tools to support their services took approximately 14 months, from March 2022 to May 2023, highlighting the complex barriers to entry in the insurance space, such as licensing and technological setup. Challenges included navigating these barriers and ensuring alignment between engineering and underwriting teams to maximize the effectiveness and adoption of their technological solutions.

What were the initial startup costs for Ledgebrook?

"- Funding: Ledgebrook raised $50 million in funding to support their operations.

What was the growth strategy for Ledgebrook and how did they scale?

Direct Customer Engagement

Ledgebrook emphasized direct engagement with their customers over conventional marketing campaigns. Their primary acquisition strategy revolved around forming strong relationships with wholesale brokers, which are their main customers. The company prioritized in-person meetings and constant communication. Underwriters frequently traveled to various cities like Chicago, Atlanta, and Philadelphia to meet brokers, building trust and ensuring a solid relationship. By maintaining open lines of communication and by consistently delivering quick and reliable service, they secured and retained their initial customers.

Why it worked: In the B2B insurance sector, where personal relationships are crucial, face-to-face interaction with partners built credibility and trust, proving more effective than traditional marketing. Their strategy of being the "easiest to deal with" resonated with brokers who are accustomed to slow, bureaucratic responses from traditional insurers. This direct engagement ensured that brokers preferred working with Ledgebrook due to their swift quote system and consistent communication, which set them apart from competitors.

Technology Integration

Ledgebrook’s tech-driven approach plays a vital role in their ability to pull in business and provide quick turnaround times for quotes. They've invested in a proprietary tech stack that integrates both modern technology and insurance expertise. They've automated many "micro-tasks" using artificial intelligence to streamline processes, which helps remove internal barriers and allows their underwriters to focus on core activities. Tech team members also participate in regular "ride-alongs" with underwriters, ensuring products are fine-tuned to actual customer needs.

Why it worked: By efficiently integrating technology with traditional insurance practices, Ledgebrook handles broker submissions more swiftly and accurately than many competitors. This means data is processed rapidly using third-party sources and delivered to underwriters, resulting in being first to offer quotes to brokers. This level of responsiveness helps build two key aspects valued by their broker partners: speed and consistency.

Employee and Referral Growth

Ledgebrook has experienced rapid staff growth by leveraging a workplace culture that fosters enjoyment and productivity. Much of their team growth actually originated from employee referrals. Employees who enjoy their work environment at Ledgebrook have been known to refer talented friends and former colleagues to open positions, allowing the startup to more than triple in headcount within a year.

Why it worked: A positive and engaging work environment can become a powerful recruitment tool. Employees who enjoy their work environment are more likely to recommend friends, making referrals a key strategy in the company's rapid scaling. This network effect reduces hiring costs and ensures a compatible team culture.

Strategic Use of Conferences

Aside from the digital and direct engagement tactics, Ledgebrook also capitalized on industry events to build new relationships and bolster its reputation. They attended key industry conferences, allowing them to expand their network and gain further recognition. Many professionals in the industry had worked with their team, including new hire, Steve Mills, a respected figure with substantial industry experience. These connections were instrumental in building trust and expanding their reach in the wholesale broker market.

Why it worked: Face-to-face meetings and maintaining active, regular contact with their broker partners helped establish trust and fostered long-term relationships. This strategy effectively addressed the traditional insurance market’s slow pace and the barriers startups often face.

External Partnerships

Strategic partnerships have played a crucial role in Ledgebrook’s growth and ability to deliver top-notch products to their clients. One notable partnership is with Secotra, which provides Ledgebrook with a modern policy administration system. This tool offers the flexibility to build and deploy new products rapidly, a necessity given the fast-paced nature of the insurtech and commercial insurance markets.

Why it worked: The collaboration with tech-driven service providers like Secotra helped build a robust technological foundation for Ledgebrook, allowing them to be agile in launching additional insurance products like Professional Liability and Unsupported Excess offerings. This ability to quickly bring new products to market enabled Ledgebrook to swiftly scale to a $100 million run rate just 19 months after writing their first policy, demonstrating significant growth potential in a traditionally slower-moving industry.

What's the pricing strategy for Ledgebrook?

Ledgebrook prices its E&S insurance products using a tech-driven approach for fast and accurate quoting, offering products like General Liability and Unsupported Excess, with plans to expand product offerings.

What were the biggest lessons learned from building Ledgebrook?

Speed Matters: Ledgebrook found success by promising the fastest quotes to brokers, valuing speed over being the cheapest. For startups, focusing on delivering a few critical advantages can differentiate you from established players.
Direct Engagement Beats Flashy Marketing: Ledgebrook prioritized in-person interactions with brokers, proving that building relationships can be more effective than traditional campaigns. Aspiring founders should consider how personal connections can drive business success.
Consistency Counts: By continually delivering on promises, Ledgebrook built trust and reliability in a field where others often falter. Demonstrating consistent service can be a powerful way to establish and maintain credibility.
Integrated Teams Drive Innovation: Ledgebrook encourages its tech team to experience client interactions firsthand with underwriters, ensuring their solutions meet real-world needs. Founders should foster collaboration between technical and customer-facing teams for better product development.
Referral Recruiting Fuels Growth: The company scaled its workforce through employee referrals, creating a culture where staff are so satisfied they recommend it to friends. Building an enjoyable workplace can significantly enhance your talent acquisition strategy.

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