Ladder: Reimagining Life Insurance
Highlights from ✨Hot Deal Time Machine✨⏳ -- On Clubhouse
Below are highlights from my recent Clubhouse episode featuring Jamie Hale, CEO and Co-founder of Ladder, and Brendan Dickinson, GP at Canaan and Series A investor in Ladder.
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🔮 The Vision: Rebuilding the tech stack for life insurance
From day one, Jamie Hale and his co-founders set out to completely reimagine life insurance to provide a simple, fast, and affordable product for consumers. For Ladder, this meant completely rebuilding the tech stack for everything that touches the consumer: how customers discover the product, how they submit an application, how the policy is underwritten, and how the policy is issued and bound. While this tech-first approach had been established within the world of credit, it was revolutionary within life insurance at the time - in which most companies followed an agency model selling 3rd-party products. While the work of rebuilding the industry can be difficult and slow-moving, it also provides many more levers to control product and distribution as the company matures. Today, Ladder is seeing the fruits of that investment with their comprehensive coverage across states and amounts from $100K to $8M, as well as their ability to partner deeply across the FinTech ecosystem.
📡 The Early Signal: Partnerships before product
At the time of the Series A, Ladder was still pre-product and pre-revenue. While they had done some experimentation on the agency side to understand the customer problem, they did not yet have a product or experience that could be user-tested. Where they had spent time was building “below the waterline” - a term used to describe Ladder’s underwriting stack, or how they sort and price risk. In doing this, the company spent significant time talking to reinsurers and carriers that they brought on as partners. For Dickinson, these partnerships were meaningful enough to convince him to lead the Series A. At the time, these types of partnerships were unique - and were a major validation point that a large insurance incumbent was willing to take the risk that was generated by a small start-up and it’s underwriting algorithms.
👫 The Leadership: A husband-wife team
Partnering with a spouse or family member to start any company can be a tricky task, let alone a start-up with ambitions of becoming a category defining business. And VCs and employees alike may worry about favoritism or personal squabbles bleeding into the professional setting. In fact, Hale recalled that many VCs passed on the opportunity to invest in Ladder in the early days, specifically because they they were a husband-wife team. That said, Jamie and his wife Laura, two of the four co-founders of Ladder, seemed to have figured out a way to turn their relationship into a thriving professional partnership. The secret? Candor woven into the culture of the team. Jamie shared that every co-founder relationship is unique and fundamentally relies on communication. Given the nuances of a husband-wife co-founding team, Jaimie says they talk about their leadership dynamic very directly with every senior exec hired into the organization. By continuously speaking openly about both the good and the bad in the company, no matter who is involved, a culture of honesty has been instituted that enables the entire team to move forward effectively.
🪒 The Inflection Point: Policies you can complete while shaving
Hale describes the first time he felt that Ladder was on its way to becoming a big business: when he could go to sleep at night and wake up in the morning and have new policies completed - without any manual intervention. While this was still early days for Ladder, it was a definitive point for the company when the infrastructure they had spent endless hours building was now running the company. The full lifecycle of a policy - from customer acquisition to issued policy could run across Ladder’s proprietary tech stack. For Hale this demonstrated his initial vision of a simple, fast, and affordable product for consumers was possible - opening up endless possibilities to launch Ladder into a business of significant scale. In fact, one of Hale’s favorite stories is of a dad who literally completed his life insurance policy while shaving. It just worked - everything a typical young millennial father has come to expect when transacting online.
👉🏼 ✨Hot Deal Time Machine✨⏳ is a 30-minute Clubhouse show where we travel back in time to the early stages of some of today’s hottest deals. Hear from founders and investors on the original pitch and thesis…and how things actually played out