Fintech
Jun 10, 2021

Don’t Move Twenty Footballs One Yard, and Other Advice from Policygenius Cofounder Jennifer Fitzgerald

New Yorkers might know Policygenius from its subway advertising campaign, which put the parlance of the MTA’s Poetry in Motion series into life insurance ads. 


This kind of outside-the-box thinking has defined how startup challengers can set a whole new tone for dusty industries like insurtech. So has Jennifer Fitzgerald, CEO and cofounder of Policygenius. The McKinsey & Company management consultant with a background in standup comedy and the Peace Corps didn’t have a standard startup resume, and brought her idea to market well before insurtech was an established industry. Here, she tells Katheryn Thayer how her team pushed on to raise over $100 million, helping more than 30 million people shop for all kinds of financial protection, from life and home insurance to wills and trusts. 

What’s the Policygenius origin story? What made this concept exciting to you? 

My cofounder Francois de Lame and I met as McKinsey consultants advising major insurance firms in the early 2000s. Many of our insurance clients were struggling to connect with modern-day consumers, especially after the 2008 financial crisis. The market was changing; insurance had predominantly been sold by brick-and-mortar insurance agents in the past, but in an increasingly digital world, many people didn’t have in-person relationships with insurance agents anymore. We saw a big opportunity to bring modern digital convenience to the process of shopping for insurance, and that’s where the idea for Policygenius began. Today, it’s amazing to look back and see how much our company has grown: we’ve helped millions of people shop for insurance and placed more than $100 billion in coverage. 

What’s a key piece of early advice you’d want to give a new fintech founder on day one? 

The fastest way to kill a startup, especially in the early days where resources are so limited, is to try to do too many things at once and wind up not doing anything particularly well. You have to focus on finding and leaning into your product-market fit. Internally, we’ll say you don’t want to move twenty footballs one yard; you want to carry a football into the endzone, and then do it again and again. When we started out, we were laser focused on creating an amazing experience for life insurance. Because of our focus on creating the best possible customer experience for life, we were able to tap into a lot of unmet demand in the market – fast forward to today, and we’re one of the biggest players in life insurance. We’ve since expanded into other products like home and auto insurance and estate planning, but that early laser focus really set us up for success. 

What’s the biggest challenge you’ve overcome as a founder so far and how did you do it / what did you learn?

Getting consumer attention in insurance is probably more difficult than for any other product. It’s not a fun or physical product, it’s extremely expensive, and the space is crowded with big brands who spend billions of dollars on advertising each year. Breaking through as a startup was very tough—and this was especially true in the days before the insurtech boom, when no one was really thinking about disrupting insurance. We’ve gotten creative on many occasions to build our brand, like running a tongue-in-cheek poetry subway campaign that wound up getting a lot of attention. We’ve also made big investments in free online content and consumer education, which has become a cornerstone of our brand and taught me that even if the payoff takes a little longer, it’s worth investing in resources that can help you build trust with your customers.

What’s one thing you learned as you did your first few seed-round pitches? What do you think investors most want to see from fintech founders at this stage? 

Raising capital was hard in the early days. This was before the insurtech boom, and we had a hard time convincing institutional investors of the opportunity here. It was also harder because we were first-time founders, without a successful startup brand name on our resume. So I learned the importance of persistence. When we were getting nos from everyone, I still believed in what we could build here, so we turned to friends and family and ultimately were able to raise around $750,000 that we stretched for two years. It became easier to fundraise after that, but I still credit those early challenges with building a scrappiness in our company’s DNA that has served us well over the years.

What kinds of early hires are most important in this industry? What kinds of characteristics and backgrounds should they have? And how did you approach finding them? 

Getting the people right has always been incredibly important to me. From the early days at Policygenius, we knew we wanted to invest in our people function as a strategic function of our organization. Our head of people was our 20th hire, far earlier than most startups hire for the HR function, and that early investment in getting our values, recruiting, and development philosophy right was crucial to building the powerhouse team we have today. Early hires should be values-aligned above all else, because the culture you build early on is the culture you’ll have forever. 

What was a key turning point in discovering your product-market fit? What kinds of questions do you suggest fintech founders ask themselves to get here? 

One of the best ways to learn quickly is by trying to sell your product to customers. 

In the early days, my cofounder and I worked together as sales reps on the phones. For two years, while we were building the product, fundraising, and recruiting, we were also taking phone calls and advising customers. That gave us a very strong foundation in understanding what our customers wanted. We learned that trust was paramount, especially for a big expensive decision, like purchasing insurance. We learned that while digital convenience and self-service is important to a modern shopper, there’s no substitute for talking with a human expert at the moment of truth. When people are taking the plunge to buy a policy, they want to have that human touch to feel comfortable. That mix of digital convenience and human support set us apart in the early days and still sets us apart today.

What are a few key documents and/or processes you’d suggest founders focus on at early stages? Tips for making them most effective?

One piece of advice I’d suggest to any founder is building your network. Having a peer network of people who are trying to do the same thing you are but are a little farther along is invaluable. I’ve met with a group of CEOs of similar-stage companies at least once a month for years. Whether it’s for a tactical question or simple sanity check as you’re starting out, having that group of people to turn to is key. 

What fintech trends or predictions are you thinking about most right now?

I’m thinking about consolidation in financial services—basically every fintech company is trying to become the platform for something, and you’re seeing a lot of pivots and horizontal and vertical expansion. It’s a changing chessboard, for sure.


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