Jennifer Fitzgerald is the CEO and Co-Founder of Policygenius, an online insurance marketplace. Previously, she was a junior partner at McKinsey & Company, where she advised Fortune 100 financial services companies on marketing and strategy. As one of only three female founder CEOs to have ever raised more than $50M in funding for a fintech startup in the US, Jennifer regularly shares her insights on personal finance and insurance tech and serves as an expert on the insurance industry and the entrepreneurial path. Her articles have appeared in TheNextWebEntrepreneur Magazine and Huffington Post and she has been quoted as a source in The Wall Street Journal, The New York Times and She is a graduate of Columbia Law School and Florida State University. 

1. How has your life experience made you the leader you are today? 

I grew up in a military family, meaning we moved around a lot and I was frequently the new kid in school. That made me resilient to change and able to integrate into new situations quickly, which is important for a leader to be able to do. It also made me empathetic to how people feel during situations of change — like when a new employee joins my company — which made me more mindful of organizational planning and onboarding.


2. How has your previous employment experience aided your current role?

Before starting my company, Policygenius, I was a management consultant at McKinsey & Company. In that role, I worked on difficult business problems for our clients — everything from strategy to operations. It made me an efficient problem-solver and exposed me to the full spectrum of challenges a business can face, ultimately helping make me a more well-rounded CEO and leader.


3. What have the highlights and challenges been during your current role?

The biggest highlight has been driving incredible growth. We started as two people with an idea, and are now an actual company with more than 130 employees, all happening in just a few short years. That has been so rewarding to be a part of. Probably the biggest challenge has been to stay emotionally balanced during this rollercoaster ride.


4. What advice can you offer to women who want a career in your industry?

I’d advise women who want a career in entrepreneurship to seek out a range of business experiences. You’ll want exposure to operations, finance and management. You’ll want to work for good managers, so you know how to role model those behaviors for your future employees.


5. What is the most important lesson you’ve learned in your career to date?

 That you have to put in the work, and be persistent and resilient if you want to accomplish anything of importance. You can’t control how lucky you are, or what talents you’re born with, but you can control the hours you put in.


6. How do you maintain a work/life balance?

 It’s not easy to do when you run a company — and you have to go into entrepreneurship and leadership knowing that you’ll be working harder than you would in other roles. But if you work with people you like, and take time to celebrate even the smallest wins, the work/life balance feels manageable.


7. What do you think is the biggest issue for women in the workplace?

 Probably the biggest issue is that there aren’t enough women in leadership roles. The pipeline of women candidates gets smaller and smaller the higher up in a company you go — and unfortunately that’s a challenge with no easy solution.


8. How can we encourage more women to start their own business?

 We can encourage more women to start their own businesses by highlighting more success stories in the media of those who’ve done it — this shows it can be done! And I’d encourage women entrepreneurs to reach out and be helpful to aspiring women entrepreneurs.


9. How  has mentorship made a difference in your professional and personal life?

 Mentorship has been so important in my career. The encouragement, advice and support you get from a mentor is so helpful, especially during critical decision points in your career.


10. Which other female leaders do you admire and why?

 Indra Nooyi, the CEO of Pepsi, is a female leader I’ve long admired. She led Pepsi through a strategic redirection, which is no easy feat for a company that large. And in interviews I’ve seen of her, she comes across as warm, humble and no-nonsense. They’re not famous, but I also had really great female managers at McKinsey who set me up for success early in my career.


11. What do you want to professionally and personally accomplish in the next year?

 Professionally, I’d like to see my company, Policygenius, continue to grow and move into new product verticals. Personally, I’d like to be able to accomplish my professional goals while also keeping my stress to manageable levels!


12. What are the top three tips you can offer to an entrepreneur starting out?

 The three tips are find, focus and surround. First, find another entrepreneur who is about 12 months ahead of you in the process to give you advice on what you’re working on. Then focus on your customers and what problem you’re solving for them. Ultimately, this is what success for your business boils down to. Finally, surround yourself with great people. You’ll want employees who are not only talented, but who have high-integrity and positive attitudes.

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