Gage Caligaris, CEO & Founder of Ledgebrook: $50 Million Raised to Revolutionize Commercial Insurance Technology

Ledgebrook is transforming the commercial insurance industry with a technology-driven approach that prioritizes speed and service for wholesale brokers. With $50 million in funding, the company has rapidly scaled to a $100 million run rate in less than two years since writing its first policy. In this episode of Category Visionaries, I spoke with Gage Caligaris, CEO and Founder of Ledgebrook, about his journey from spending nearly a decade as an actuary at Liberty Mutual to launching an insurtech startup focused on making commercial insurance quoting faster and easier.

Topics Discussed:

• Ledgebrook's mission to bring faster quoting experiences to wholesale brokers
• The 14-month journey from founding to writing their first insurance policy
• Scaling from 30 to nearly 100 employees in just one year
• Reaching $100 million run rate within 19 months of their first policy
• The company's expansion strategy of rapidly launching new insurance products
• Building a distributed team culture that remains connected and engaged
• The E&S (Excess and Surplus) insurance market opportunity exceeding $100 billion

 

GTM Lessons For B2B Founders:

• Simplify your value proposition: Ledgebrook succeeded by focusing on two clear promises: being the fastest to quote and the easiest to do business with. Gage explained, "Fast and cheap is what they like. We'd prefer to be fast over cheap." B2B founders should identify the 1-2 most critical pain points in their industry and build their entire value proposition around solving them.
• Choose boots-on-ground engagement over flashy marketing: Despite their rapid growth, Ledgebrook has minimal formal marketing. Instead, their underwriters travel two weeks each month to visit brokers in person. "We're in our broker's offices... instead of a marketing campaign, it's a boots on the ground approach," Gage shared. For B2B startups, prioritizing direct customer engagement can be more effective than traditional marketing campaigns.
• Maintain consistent service delivery: Ledgebrook built their reputation by simply delivering on their promises consistently. "We kept showing up, right? We kept coming back with those fast quotes, we kept picking up the phone," noted Gage. B2B founders should recognize that reliability and consistency are powerful differentiators in markets where competitors often overpromise and underdeliver.
• Integrate customer-facing and technical teams: Ledgebrook has tech team members do regular "ride-alongs" with underwriters to see how their products are actually used. This collaboration ensures they build the right features and move faster. B2B founders should create structured opportunities for engineers and product teams to directly observe customer interactions.
• Leverage referral recruiting for growth: Ledgebrook has scaled their team primarily through employee referrals. Gage shared, "People are like, man, I'm having a blast here. Let me bring my friends." Creating a workplace where employees genuinely enjoy their work can transform your hiring process, especially when scaling rapidly.

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