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Jennifer Fitzgerald of Policygenius: “You cannot over-invest in finding and retaining the best people”

One of the most important things any leader needs to do is to distinguish between what’s truly important and urgent versus what you can delegate. Once you have a large team, you have people to delegate even some of the urgent important things to, which can be a challenge. But doing so ultimately gives you […]

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One of the most important things any leader needs to do is to distinguish between what’s truly important and urgent versus what you can delegate. Once you have a large team, you have people to delegate even some of the urgent important things to, which can be a challenge. But doing so ultimately gives you the opportunity to focus on the things only you can do. Of course, this requires that you hire the right leadership team to support you — and this is probably the most important thing that you can spend your time on. You cannot over-invest in finding and retaining the best people.


As a part of my series about strong female leaders, I had the pleasure of interviewing Jennifer Fitzgerald. Jennifer is the CEO and co-founder of Policygenius, one of the nation’s leading online insurance marketplace. She is the Ernst and Young Entrepreneur of the Year New York 2019, one of Fast Company’s 100 Most Creative People in Business for 2018 and is one of only four women founders in Fintech to raise more than $50 million in funding. Before starting Policygenius in 2014, she and her co-founder, Francois de Lame, were management consultants at McKinsey & Company. Jennifer has shared insights in major publications including The New York Times, The Wall Street Journal, Bloomberg and more. Early in her career, she was a Peace Corps volunteer and did standup comedy. Jennifer is a graduate of Columbia Law School and Florida State University.


Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path?

I started my entrepreneurial journey in the Peace Corps. I was stationed in Honduras and worked with a local municipality lacking funds for basic government functions. From there I went on to be a consultant at McKinsey & Company, advising top financial services companies, national insurers and wealth managers on marketing and strategy. While there, I met my Policygenius co-founder Francois de Lame. Together we discovered there was a big disconnect between traditional insurance and digital consumers — and we both had this lightbulb moment realizing we could fix that, which is where the idea of Policygenius began. We went from being the two of us and our dog Ruby in 2014 to recently celebrating our fifth anniversary with over 220 employees.

Can you share the most interesting story that happened to you since you began leading your company?

It might not be the most interesting story, but certainly the most exciting thing for me, even now, is to meet strangers who, when I tell them what I do, say they’re a Policygenius customer. That still floors me — that this company we created out of thin air is out there in the world, and that people trust us with important purchases!

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

When we were naming our company, we actually started with a different name, KnowItOwl. We thought the pun was clever, as our company has an advice and educational component. But we soon realized it wasn’t going to work. People kept asking us to spell the name and explain it, so we knew we had to pivot. We ultimately went back to the drawing board, working with our growing team to brainstorm ideas. After tossing out some names we knew weren’t right — by pulse checking if we’d be embarrassed to say to a reporter and if the domain wasn’t available — we ultimately got to Policygenius. It was good for us to learn early on the importance of checking with our audience to make sure we’re doing the right things, which we continue to do in several aspects of the business today.

What do you think makes your company stand out? Can you share a story?

Policygenius is the leading online insurance marketplace. We have rapidly grown our life and disability insurance business since we started in 2014, and we’re now a top 3 player, nationally. We expanded into the home and auto verticals earlier this year and, around that time, I reflected on all we’ve done and what’s to come. One thing I think we’ve found the secret sauce to is our 80% digital, 20% human approach. It helps consumers own the process until they need help at any moments of truth. This is applicable through our all verticals and something we are proud of.

Are you working on any exciting new projects now? How do you think that will help people?

One of the big trends we’re seeing in fintech is bringing back the human touch to things that have gone completely digital. As I mentioned, this is something I think we do really well. We are at the forefront of this trend because we’ve always kept an emphasis on how our customers want to engage with us. As we continue to grow and improve our processes, we’ll keep talking with our customers to make sure we’re providing service that’s truly benefit them and sticking with the Policygenius mission: Get people the financial protection they need and help them feel good about it.

What advice would you give to other female leaders to help their team to thrive?

One piece of advice I would give to other women leading teams is to stay positive and optimistic. Particularly in the early stages, building a new business can be difficult and discouraging, but it’s your job as a leader to keep everyone motivated — and this spans to both investors and employees.

What advice would you give to other female leaders about the best way to manage a large team?

One of the most important things any leader needs to do is to distinguish between what’s truly important and urgent versus what you can delegate. Once you have a large team, you have people to delegate even some of the urgent important things to, which can be a challenge. But doing so ultimately gives you the opportunity to focus on the things only you can do. Of course, this requires that you hire the right leadership team to support you — and this is probably the most important thing that you can spend your time on. You cannot overinvest in finding and retaining the best people.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

A lot of people have been instrumental in getting to where I am, but I wouldn’t have been able to create Policygenius and get it to where it is today without my co-founder, Francois de Lame. We’ve built this company together and it’s been great having someone along for the ride with me. Between initial fundraising where we had our friends and families as early angel investors to our current roles, we’re going through it all together. But we’ve built a support system around us as we’ve gone along and it’s all played a vital role into shaping the Policygenius you see today.

How have you used your success to bring goodness to the world?

Policygenius is there for people at moments of truth — from a flood that destroys your home to an injury that puts you out of work. The financial instruments Policygenius provides bring people a sense of security and peace of mind that they won’t be left in financial ruin when life gets tough.

Outside the insurtech space, I also participate in the Inc. Founders Project, where I mentor an up-and-coming entrepreneur. I’ve had a number of inspirational mentors in my life, and am happy to be in a place where I can give back after receiving guidance from mentors of my own.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

1. The first 12 months will be a blur, and if the company survives that phase, you’ll want memories of it. Take more photos and document important milestones!

2. Figure out a good hiring process early on, because getting a few good people in the door quickly will make a huge difference.

3. Be ruthless about how you prioritize your time in the early days — a lot of things will seem super important but most of them aren’t.

4. Build a solid peer network as soon as you can, and tap into them for advice early and often to sidestep avoidable mistakes.

5. If you stay laser-focused on solving real problems for a real customer, then the score will eventually take care of itself.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

The world can never have enough kindness and empathy. As I’ve gotten older and further in my career, I’ve come to learn that these are such important qualities for success in both the workplace and your personal life. Everyone should make it a regular practice to put themselves in the shoes of the person they’re interacting with — it will go a long way to building trust-based relationships.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

I’m a lifelong San Antonio Spurs fan and their head coach, Gregg Popovich, instilled the team mantra “pound the rock.” This phrase encourages you to stay persistent in tough situations. As an entrepreneur, this can come into play throughout your journey, from getting initial funding to expanding your business.

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them 🙂

Like I said, I’m a big Spurs fan, so I’d love to sit down and chat with Coach Popovich. He’s built such a respected team and motivates people beyond the players on the court.

Thank you for all of these great insights!

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