Editor’s Note: This is part of What She Learned, a new interview series with successful women entrepreneurs about their journeys and the lessons they learned along the way.

Jennifer Fitzgerald, co-founder of Policygenius, is unassuming in manner but obviously driven. (Credit: Courtesy of the company.)
Jennifer Fitzgerald, co-founder of Policygenius, is unassuming in manner but obviously driven. (Credit: Courtesy of the company.)

It’s clear that Jennifer Fitzgerald, co-founder of Policygenius, a buzzy new insurance platform aimed at millennials, isn’t afraid of shaking up a traditionally stodgy industry.

When I arrive at her startup’s Insta-worthy new office space in New York’s Flatiron district, I’m greeted by a friendly one-eyed dog name Wink. A receptionist in skinny jeans and an oversized sweater directs me to a shiny white kiosk, where I tap out my name and click a few boxes. I’m puzzling over whether I’ve just ordered a latté or signed a non-disclosure agreement (turns out, the latter) when the company’s enthusiastic media relations manager, Brooke Niemeyer, who wears a rockabilly headband — bounds over. She escorts me to the Stanley Kubrick conference room, where Fitzgerald and I will chat over apple-flavored seltzer water.

Fitzgerald, dressed in jeans and a plaid shirt, is the CEO of a 4-year-old venture that’s raised about $60 million in financing and was recently valued at $130 million. The hipster ethos of her office — I spot a worker with a poop emoji sculpture on his desk — reflects the company’s calculated strategy to appeal to an iPhone-addicted demographic that doesn’t have the time (or inclination) to meet face-to-face with an agent to buy life, auto, renters, health or pet insurance. Fitzgerald, who is unassuming in manner but obviously driven, gets right to the point.  “When somebody thinks about insurance or financial protection,” she says, “I want them to think of Policygenius, and not Allstate or Northwestern Mutual.”

It’s an ambitious goal to disrupt an old, regulated, messy industry like insurance — and Fitzgerald claims (rightfully so) to be a pioneer in what is now called “insuretech.” The term applies to startups using technology to modernize insurance. Five years ago, when she and Francois de Lame quit their jobs at management consulting firm Mckinsey to build out their concept for Policygenius as an Expedia-like platform for one-stop policy shopping, “nobody was really thinking about insurance,” she says. “And now it’s a big thing.” In fact, an annual InsureTech Connect conference, held this past October in Las Vegas, now attracts some 6,000 attendees.

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While at McKinsey, Fitzgerald and de Lame noticed a pattern: Their clients who were old-school insurers consistently struggled with how to engage with digital-native customers. Research indicates that young consumers — unlike Baby Boomers or older generations — are OK with buying insurance online and in fact, want to comparison-shop policies via the Internet. It was a “light bulb moment,” says Fitzgerald. Confident that their idea for a digital marketplace would work, Fitzgerald and de Lame exchanged steady corporate paychecks for the high-stress stakes of startup life, and set about raising money.

An Uphill Climb

When I first shake hands with Fitzgerald inside the glass-walled conference room, I’m surprised how different she looks from the photos I’ve seen splashed across Inc., Forbes and the New York Business Journal. I think it might be the rather dramatic highlights streaked across her brunette bob. “These are new-ish,” she confirms. “I’m very lazy [about salon visits], but you’re just catching me very shortly after a hair appointment.”

The fact that Fitzgerald doesn’t look like your typical tech-bro entrepreneur — or for that matter, someone in insurance — made it tough for Policygenius to win early-stage capital. “Investors didn’t get it,” Fitzgerald says. “We didn’t look like your typical co-founder team.” De Lame is a white guy originally from South Africa, who likes cricket. “We had one man, one woman, both of us ex-consultants, neither of us software engineers — we basically had every strike against us.”

After a frustrating 4 months, during which they fruitlessly pitched over 100 investors, Fitzgerald and de Lame decided to change tack. Appealing to friends and family, they raised $750,000 in early seed money — less than their goal of $1 million, but enough to keep them and a small team afloat for 18 months.

That initial rejection was tough. I ask Fitzgerald what it was like, facing all those nos. She’s a career-driven type who, by her own account, appears to have gone to top-ranked Columbia Law School for the hell of it (she had no interest in practicing law). The VC snubs were discouraging “especially coming from a path where I’d always been an overachiever,” she says. “You’re led to believe that if you just work hard enough, things will happen. We were working our tails off, and it still wasn’t happening.” She started to doubt herself.

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Women, either because of socialization or innate behavior, tend to handle rejection worse than men. Did Fitzgerald struggle more than her male co-founder, I inquire? “That was certainly the case,” Fitzgerald affirms. “I took it more personally then he did. I internalized it a lot more than he did.” It actually was helpful for her to watch how de Lame let rejection roll off his back. “He was like, ‘Let’s go pitch again, see what we can do.’”

She also dealt with sexism. In one memorable pitch, “the perspective investor kept directing his questions to my co-founder, not me, and it was just so out of the ordinary,” says Fitzgerald, who has clearly chosen to laugh about the incident (she fills the room with an incredulous chuckle). She recently told Inc. magazine about the encounter, calling it an “oh-shit-it’s-because-I’m-a woman” moment. “Thankfully,” she adds now, “that was atypical.”

After launching a first iteration of Policygenius, and signing up initial customers by reaching out to personal finance blogs, Fitzgerald and de Lame won their first investor: TX Zhuo, a former McKinsey consultant who was a managing partner at Karlin Ventures. “It was a relief because we were probably 2 weeks away from running out of cash,” Fitzgerald says. “He actually had to advance us a million of it so we could make payroll.” In total, they nabbed a Series A round of $5.3 million. After that, it got easier — when it comes to investors, “there’s a little bit of a herd mentality,” she says — and backers now include Steve Case’s Revolution, among others.

Kind of a Big Deal

These days, Fitzgerald is having something of a moment. In September, Quartz ranked her 44th on its “rising stars” list of nearly 250 female founders. Forbes has noted that she’s one of only five women in fintech (finance technology) to have raised over $50 million. CB Insights just named Policygenius to its Fintech 250 list.

Yet, she still (by choice) doesn’t have a private office. At Policygenius’s brand new open-floor-plan headquarters, which its 140 employees moved into this past summer, Fitzgerald’s desk is smack in the middle. There’s a constant murmur of noise, and youthful employees who follow the “startup casual” dress code — thick-rimmed glasses, cropped sweatshirts, pink hair, a few declarative tattoos — are clustered in stations around her desk.

She sits a short distance from the company’s “Legend” wall, which is covered with pin-up photos of staffers who have won the Michael Jackson Legend Award, sort of an alternate take on Employee-of-the-Month. The MJ award, I ask? “It’s a very weird origin,” she says. Policygenius’s first office was a co-working space in Williamsburg, Brooklyn — “like a poor person’s WeWork [without] the cucumber water” and there was a “really gross” red-and-black fake leather couch in the common area. “It kind of looked like Michael Jackson’s Thriller jacket,” she says. “I don’t know how that lead to us creating a Michael Jackson Legend Award, but there it is.”

While she was in law school, Fitzgerald took stand-up comedy courses with the Upright Citizens Brigade, and her quirky humor permeates the office. The small conference rooms scattered around the open floor plan are named after atypical “geniuses” (her idea) — there’s Betty White, Beyoncé, Oprah, Jeff Goldblum. I mention that Goldblum seems a somewhat strange choice. “I think that was an inside joke from one of our teams,” Fitzgerald admits. “I was like, ‘Guys, why?’ I like Jeff Goldblum though.”

Her own personal conference room — which nobody else gets to use, except maybe de Lame — is the Gregg Popovich room. I search my brain for who that is. Fitzgerald helps me out. “He’s the head coach of the San Antonio Spurs,” she says. A military brat, Fitzgerald lived in quite a few places before spending some formative years in Texas. She was awed by Popovich, but not because she plays basketball. “I’m very unathletic,” she deadpans. Rather, “he’s built probably the most successful sports organization, certainly in recent history, but I think of all time.” I silently wonder how many female insurance startup CEOs have an NBA coach as a role model and decide Fitzgerald is probably unique.

No Lemonade Stands

We’re close to wrapping up our interview, so I ask Fitzgerald to provide a few pointers for aspiring women entrepreneurs. One is to not be intimidated by the unfamiliar. “I didn’t run a lemonade stand as a kid, so this was a completely new path for me,” she says, of entrepreneurship. For the past 2 years, to beef up her business-ownership skills, she has participated in a program called Venwise, which assembles small groups or “pods” of CEOs in non-competitive industries for monthly boardroom-style discussions. “I’m the only woman,” she says, but “it’s super helpful.”

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Fitzgerald also makes it a habit to check out what other startups are doing, simply by being a consumer. She wakes up at 6 a.m. each morning and tries (sometimes successfully) to exercise at fitness-franchise startup Orangetheory. She orders lunch and dinner at the office using the meal delivery service Kettle Bell Kitchen, founded in 2013. And the seltzer she’s been sipping throughout our meeting is Bubly, Pepsi’s attempt to innovate in the soft-drink category. “It’s helpful to learn about how new companies … think about the user experience,” she says. “That’s a big thing.”

Improving “user experience” is why Policygenius has spent a good chunk of its budget making its site friendly in tone and helpful in terms of informative articles on personal finance, travel, raising kids, even how to make “heavenly” peanut butter cookies for less than 25 cents each. Articles are loaded with links to where one can buy insurance on Policygenius’s platform, plus searchable terms that help the site’s content rank high in Google. When Fitzgerald tells me she has about 10 people dedicated to editorial content, I mention that’s bigger than my news organization. “And we’re growing it considerably,” she adds. (Insert sad trombone noise here, on behalf of the entire media industry.)

As we leave the Stanley Kubrick conference room — we would have been in Popovich, but there was jackhammering outside — Fitzgerald mentions the best advice she herself ever received: “Get the people right.” I ask her whether that means employees’ talent, abilities or personality. “All of the above,” she says. “You need to make sure that they’ve got the right skills, the will, especially in the early days when you’re all working long hours and sitting in the same room.”

Of course, Policygenius employees are still sitting in the same room, albeit a football-field-sized one, complete with a cafeteria stocked with LaCroix and the requisite coconut water. As Fitzgerald herself escorts me to the front door, we pass rows of millennial staffers.

Fitzgerald seems to have them all in mind when I ask her, what’s your biggest success?

“At the risk of sounding obvious,” she says, “it’s this.” Five years ago, she couldn’t have imagined the company would have grown to its current size. “I usually am too busy to stop and reflect, and be like, ‘Holy cow, look what we’ve done. We have all these people here,’” she says. On the odd occasion she does stop for a moment, “I’m like, ‘wow,’” she says. “It’s very humbling.”