Neil Patel

I hope you enjoy reading this blog post.

If you want help with your fundraising or acquisition, just book a call click here.

Jennifer Fitzgerald is the co-founder and CEO of Policygenius which has developed an easier way to compare and buy insurance. Policygenius has raised to date over $50 million from top investors like Norwest Venture Partners, Revolution, Susa Ventures, AXA Venture Partners, Otter Rock Capital, and Karlin Ventures to name a few. 

In this episode you will learn:

  • Jennifer’s top advice for female founders
  • How to handle and read the no’s you are getting
  • Creative strategies to fuel growth
  • Believing in yourself when facing rejection
  • How Jennifer is practicing enjoying the journey more


For a winning deck, take a look at the pitch deck template created by Silicon Valley legend, Peter Thiel (see it here) that I recently covered. Thiel was the first angel investor in Facebook with a $500K check that turned into more than $1 billion in cash.

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The Ultimate Guide To Pitch Decks

Moreover, I also provided a commentary on a pitch deck from an Uber competitor that has raised over $400 million (see it here).

Remember to unlock for free the pitch deck template that is being used by founders around the world to raise millions below.

About Jennifer Fitzgerald:

Jennifer Fitzgerald is the CEO and co-founder of Policygenius, the nation’s leading online insurance marketplace.

Jennifer Fitzgerald 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, Jennifer Fitzgerald and her co-founder, Francois de Lame, were management consultants at McKinsey & Company.

Jennifer Fitzgerald 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 Fitzgerald is a graduate of Columbia Law School and Florida State University.


Connect with Jennifer Fitzgerald:


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Alejandro: Alrighty. Hello everyone and welcome to the DealMakers show. Today, we’re going to have a super, super interesting interview. We’re going to be talking with a female founder – super, super smart. I think that what they have been able to accomplish is remarkable. Building and scaling – it’s not easy. But what they’ve done and how they’ve done it is going to provide some light, especially in a sector that is heavily regulated. So without further ado, I’d like to welcome our guest to the show today. Jennifer Fitzgerald, welcome to the show.

Jennifer Fitzgerald: Thank you. Thank you for having me.

Alejandro: So originally born in the Philippines, but I understand that you did travel quite a bit. Tell us about being born and raised there.

Jennifer Fitzgerald: Yeah. I was born there on an air force base. My dad was in the air force for 20 years. He met my mother in the Philippines, so that’s where my journey started. We lived there for a couple of years. To be honest, I don’t remember because we left when I was very, very young. And then after that, grew up on a string of air force bases across the U.S. everywhere from Mississippi to Texas. I graduated from high school in Virginia. Since then, I’ve been in Florida, Central America, and then New York for the last 15 years. With the exception of my adulthood in New York, I’ve been all over the place.

Alejandro: Wow. How was it for you to not have like one place with your friends and all of that. What kind of impact did that have for you?

Jennifer Fitzgerald: I think having met a lot of fellow military brats and moved every few years, it can either be a super positive thing, or it can actually be pretty stressful depending on how you react to it. For me, I loved it. It caused me to be resilient, to be able to adapt to new situations, meet new people, and just at an earlier age I was far more comfortable with who I was and my place in the world, just because I had to reevaluate it every few years.

Alejandro: Got it, and you went to college in Florida. Is that right?

Jennifer Fitzgerald: I went to college in Florida. Go Seminoles, and then law school in Columbia.

Alejandro: Very cool. So why did you think that it would be a good idea, and this comes from a recovering lawyer. I’m still seeking therapy. [Laughter] Why did you think it was a good idea to go after law?

Jennifer Fitzgerald: I was deciding between law school and business school after spending a few years in Central America. I decided to go to law school. 1) I thought the degree would be a bit more useful than an MBA – no offense to your MBA listeners. 2) I’m all about optionality and keeping doors open. And with a law degree, you could either go the law route or the business route, and that optionality I liked.

Alejandro: And you chose to study this, but before this, you actually did a little bit of time in the Peace Corps and then also in The World Bank. Any lessons learned or highlights from these two chapters in your professional life?

Jennifer Fitzgerald: Yeah. It was amazing. I spent four years overseas being basically the only American around. So it forced me to live and work in another language, another culture. Again, just part of the steam of me pushing myself into new environments. I often like to talk about the Peace Corps as my first entrepreneurial experience. For folks who aren’t familiar with it, it’s two years of service in a developing country. You live and work at the level of your counterparts there in the local society. So I was assigned to work with a mayor and a local government in Western Honduras. You land there, and you’re basically on your own for two years. And you have to work with your counterparts there to figure out what you’re going to work on, what’s going to deliver the most impact. Interestingly, the thing that I worked on for two years was building a software system for a municipal government there. They didn’t have a lot of revenue. It’s a very poor country, and the opportunity that I spotted was to turn their paper-based tax collection and info-management system into a very rudimentary local area network and software system that I duct-taped together using the Microsoft Suite of products. I’m not technical, and still am not, but was able to put something together that delivered a lot of impact for them. And for a split second after my Peace Corps service, I thought, “Huh. I wonder if I could turn that into a business and sell the software to other local governments.” That was back in 2003 before SaaS was really a term. Then I was like, “That seems like a crazy idea,” and I went and worked for the World Bank for a few years.

Alejandro: Very cool. Were you frustrated with how things in these types of organizations move so slowly?

Jennifer Fitzgerald: Yeah. In the World Bank, I had a terrific experience, and the people there are so, so, smart and very mission-driven. But it is a very big bureaucracy, and it takes months and months and months to work on something, get it approved, get it implemented. I think the thing that drove me from working at an institution like the World Bank to moving to the private sector was speed and the ability to drive impact faster and on a potentially bigger scale.

Alejandro: Let’s talk about the journey after law school. What did you do?

Jennifer Fitzgerald: After law school, I decided not to work in the law, and I wanted to work on the business side of things. So I joined McKinsey as a consultant.

Alejandro: One of the things that I see a lot as a repeated pattern is that a lot of founders come from consulting. Why do you think that’s the case?

Jennifer Fitzgerald: I think because you get exposed to a wide variety of industries and a wide variety of functions in a short amount of time. So you get a bit of a taste of strategy. You get some experience in operations. You get some experience in marketing and distribution. Oftentimes you’ll work across industries. So I think it gives you the ability to look at something at a 20,000-foot view and a 20-foot view. And it gives you a sense for “Huh. Maybe I could go start my own company because I’ve at least dabbled a little bit in a bunch of different industries and a bunch of different functions.

Alejandro: And here is actually where you got the inspiration. You got the introduction to the insurance industry. There were obviously different companies that you were probably consulting with, and perhaps one of the companies touched this space, and you saw something. What did you see?

Jennifer Fitzgerald: I worked for several insurance companies at McKinsey. My very first engagement, as a matter of fact, was with a big life insurance company, and I was in their back office of Operations, trying to find ways to cut costs because this was the height of the 2008 financial crisis. My very first experience at McKinsey was in the insurance industry. I did a lot more insurance engagements after that. I think there were a few lightbulb moments for me and my co-founder, who was also a consultant at McKinsey. One was, we were getting hired by all the big insurance companies to tackle some flavor of the same question, which is, how do we think about growth and capture more market share when the market is quickly changing underneath our feet? If you look at how insurance is distributed in America, it is still predominantly delivered by brick and mortar insurance agents. Those agents are getting older; most people don’t have face-to-face relationships with an insurance agent anymore. That confluence of factors together led us to spot an opportunity to create what would eventually become Policygenius.

Alejandro: So you met also your co-founders. Why do you think that, in this case, you guys saw each other as the potential good fit, or the good marriage for a potential business opportunity to have?

Jennifer Fitzgerald: I think part of it is just the blinding optimism that you have to have as a founder and entrepreneur to believe that things are going to work out and that both of you are a good fit to be co-founders. We worked together quite a bit at McKinsey, so I think we had some familiarity with working with each other. We spoke to a lot of friends and friends of friends who are founders a bit further along on the journey to get a sense of what it’s like, the discussions we need to have as co-founders before we get into it. There was a lot of hand-wringing and soul-searching before we both took the plunge.

Alejandro: What kind of discussions did you guys have?

Jennifer Fitzgerald: The first one, like who’s going to be CEO? What did we want to get out of it? What does success look like for both of us? How do we think about splitting up the responsibilities if and when we get to the point that there’s just more than two of us sitting at a table working on something? It is a lot like a marriage, and I think the advice that you see for marriages is, have the tough conversations upfront. For a marriage, it’s like kids, money, politics, religion. And for co-founders, I think the tough topics are: who gets to make decisions? What does success look like for both of you? Is there going to be an eventual power struggle over who gets to be CEO? What happens if one person wants to sell and the other person doesn’t? Those sorts of things are what we had upfront, which I think helped quite a bit for us.

Alejandro: I know that the CEO discussion is a tricky one. So how did you guys tackle this discussion?

Jennifer Fitzgerald: I think the thing that made it easier for us is 1) I was more senior than him at McKinsey, and I was actually his manager at McKinsey. 2) I think the skillset for being CEO, a lot of which is being public-facing and being a good storyteller to investors and the media is something I do naturally well, and it’s something he doesn’t like doing. 3) The third piece was neither of us has a lot of ego. We just wanted to build a really great company that served a lot of people. So I don’t think you saw the ego-dynamics that sometimes befalls other co-founder relationships.

Alejandro: 110%. And I always tell founders that it’s not about who is right or who is wrong; it’s all about what is right for the business. 

Jennifer Fitzgerald: Exactly, and what’s right for the customer.

Alejandro: 100%. So you guys are exposed to the insurance industry. You start seeing all these problems. You guys start to brainstorm. What does that process look like from the minute you see the existing problem out there to the moment that you finally get a solution and you guys bring it to market?

Jennifer Fitzgerald: Sure. So for us, it was a lot of researching into the market because I think my first question, and really our first question was, does something like this exist in the market? So I think we wanted a very good sense of what is the actual problem that we’re solving. And is anybody out there solving the problem in the way that we think it should be solved? So it was a lot of market research. It was a lot of looking at different companies, how they approach the problem. It was looking at other industries where models like Policygenius exist, and not necessarily financial services. It can be in travel. It could be in consumer-packaged goods like Amazon. So we just spent a lot of time pressure-testing what the go-to-market approach would be, what the ultimate model was, talking to founders, getting initial feedback on the idea. It was just a lot of research and conversations for the first few months until we landed on what we thought was going to be the winning model and approach. Then from there, we quit our jobs and built an initial version of the website and our first product flow to see what consumers thought of it; to see if our idea that people would engage online with an independent marketplace for insurance was something that was actually going to work in the market.

Alejandro: What was the testing process like? You got this MVP like you were saying, and you were putting it in front of people. What kind of datapoints were you looking for?

Jennifer Fitzgerald: Sure. We were looking, one, for qualitative feedback, especially around the tone, the language that we used, how we talked about insurance as a product, how we presented pricing. Our first MVP – because we’re both consultants, you do what you know – was pages on PowerPoint decks. Then in the background, we were the algorithm like coming up with the prices and things like that. So our MVP was PowerPoint and Excel. Once we got enough qualitative feedback that this is something that resonated, people understood how to make an insurance decision and were ready to proceed to the next step. Then we actually found a product designer and our initial head of engineering to start building the actual digital experience.

Alejandro: For the people that are listening, what ended up being the business model for Policygenius?

Jennifer Fitzgerald: We are a managed marketplace for insurance. You can think about is like any other managed marketplace, be it Amazon or Seamless or Expedia. We match consumers who are looking to buy insurance with the insurance companies on the backend. 

Alejandro: Got it. What were the early days like?

Jennifer Fitzgerald: The early days were the two of us probably spending too much time on an initial pitch deck, and then realizing, “Oh, wait. We should probably get an MVP and an initial product in the hands of consumers sooner rather than later. So it was looking for the initial people to join the team. That was a product designer. That was our head of engineering, and quite possibly one of the best early decisions that we made, our next employee was a content producer because we suspected that investing in content SEO early would pay off dividends in the long run. It has in a big, big way. So that was a decision we made probably month one of starting the company. 

Alejandro: Why is this industry so difficult?

Jennifer Fitzgerald: Everything about it is difficult. From the macro context, it’s regulated. It’s regulated on a state-by-state basis, which means that to get licensed as a broker or licensed as a carrier, you have to deal with state-by-state. The regulation of how you can market products, engage consumers, is also done on a 50-state basis, so you have to make sure that you are in compliance for all 50 states. To bind the product and even just have products and prices, those will differ by state, sometimes by zip code. So you have to reflect that in the pricing engines and the comparative raters that you build. That’s just on an industry context. Then if you shift from the consumer mindset, nobody wants to talk about insurance. Insurance is something that’s intimidating, it’s boring, and it brings up difficult topics like death and mortality and your home burning down. So it’s a category that’s super important to consumers, but one that they inherently distrust. The consumer challenge is, how do you get people to take action in a category where they are dreading it, and they put it off like exercise and eating healthy.

Alejandro: This also sounds like a massive undertaking. What did you guys do to reduce the learning curve?

Jennifer Fitzgerald: We had a little bit of head start because we had worked in the industry at McKinsey, although, that is night and day different from starting a company and trying to sell products to consumers. The most humbling thing you can do, and probably the best way to move yourself up the learning curve is trying to sell. So for the first two years of the company, my co-founder and I were the sales reps on the phone. We were the customer-service agents. We were taking the phone calls and advising customers on their insurance decision while also building the product, recruiting a team, and raising money. There is no better foundation that you can have than talking to your prospective customers and trying to sell a product.\

Read More: David Richards On Raising $120 Million Without Venture Capital And Then Defeating A Boardroom Coup

Alejandro: What did you learn about selling a product?

Jennifer Fitzgerald: The big thing that we learned was, one, trust is paramount. Unlike other financial services verticals like lending, for example. Lending the trust equation goes: the lender has to trust the borrower and trust that the borrower will repay their money. In insurance, it’s the opposite. The consumer has to trust that the insurance company is reputable and will be around 5, 10, 15, 20 years when there’s a claim on the policy. So building that trust with the consumer is absolutely paramount. And there’s no silver bullet for building trust. It’s in all the little things. The language that they use, how many insurers that you have on the platform, how you present price, how you ask for information. There are all these little things that you have to get right to build trust with the consumer. I think the second big thing that we learned, and it’s something that made us distinctive in market, and still makes us distinctive in market is the blend of the digital with the human. When it comes to insurance, what we learned and what the backbone of our model is, is that people want it to be digital, self-service, and easy up until they don’t. At the moments of truth, which are when you have to make a claim or when you pull the trigger on buying a policy, they want to talk to an expert, and they want to have that human touch even if it’s just for a few minutes to feel comfortable that they make the right decision, and then they’re in good hands.

Alejandro: Got it. Super interesting. One thing that I saw, obviously when you were dealing in regulated environments, you’re going to need as well to get some money. Right? Because there are just so many things that you need – lawyers, you name it. How did you go about fundraising?

Jennifer Fitzgerald: [Laughs] A very difficult situation. When we started building the product, we bootstrapped for a while, but then to your point, this is expensive. It’s a regulated industry, it’s capital intensive, and because it’s direct to consumer, customer acquisition will require a lot of investment. We tried to raise a seed round of capital from seed funds and venture capitalists and couldn’t do it. Pitched dozens, nobody cared, nobody got it, nobody liked us. But we still had a lot of conviction in what we were building, so we did it the hard way, and we pitched friends, family, angel investors, friends of McKinsey Partners, McKinsey Partners themselves. And we raised a little bit shy of $750,000 from 50 individuals who are all still on our cap table, which is fun. But a lot of other companies had a similar background. I was just talking to somebody who’s familiar with Peloton, and they had to do the same thing. They raised their initial round of funding from individuals like 100 of them or some amount who are still on the cap table. So that’s what we did to start, and we were able to stretch that money for basically two years until we raised our Series A Round of capital after we had already launched.

Alejandro: What was the turning point in order to get the institutionals on board?

Jennifer Fitzgerald: I think the turning point was a couple of things. One was we were able to get some traction and show that we could build a product. We were more than just ex-consultant PowerPoint jockeys who advise on strategy and build decks to somebody who could actually build a team, build a product, get something out in market. Then two, our initials proof points around “Hey, we’re actually able to sell very complicated products like life insurance and disability insurance” through this approach and finally broke through and got the attention of institutional investors.

Alejandro: How much capital have you guys raised to date?

Jennifer Fitzgerald: We’ve raised over 50 million dollars.

Alejandro: It’s amazing. You guys have really good investors: Norwest Venture Partners, Revolution, Susa Ventures, and even some insurance companies in here. What was the journey like, of being able to get in front of these people and closing?

Jennifer Fitzgerald: It was hard and then eventually got easier, although it’s never easy because the later rounds just get bigger. So your proof points have to be that much stronger. But I think the success begets success. The other thing that happened in the industry overall is we were ahead of our time. When we got started, InsureTech wasn’t a thing. There were only a few other companies tackling insurance from a startup in tech perspective. It was Oscar, it was Zenefits, and it was us. Since then, InsureTech has exploded. There is an annual conference in Vegas that nearly 10,000 people go to. There are dozens of newsletters. There are hundreds of InsureTech companies all within the last five years. So we were a pioneer in the space. When the space started to catch on, I think that’s what created a lot of interest in us, and a lot of realization that “Oh. Those guys were onto something.” Because when we started pitching insurance five, six years ago, we got questions like, “Really? Is this an opportunity? Is there money in this?” Which seem like silly questions now, but they were questions that we got five or six years ago.

Alejandro: Was it then, investors coming to you, and were you seeing inbound interest via email, or what was that like?

Jennifer Fitzgerald: Now, yes, because I think we have now established ourselves as a leader in insurance tech, which is increasingly a bigger part of fintech overall. There are a lot of things that we have done that other companies haven’t. I think people look to us as the leader in terms of customer acquisition, particularly in creating a very strong organic SEO base. People have looked to us because we were, again, being on the forefront of trends, not just insurance, but things like podcast advertising. We’re one of the first advertisers in insurance tech and fintech to go heavy into podcasts. We went there in 2015, 2016, and a lot of the big podcasts we’ve locked up explosivity for our category because we’ve been there for a few years. We were the first to go to the personal finance blogging community. There were a lot of other companies from the credit, lending, wealth-side of things. We were the first insurance-oriented company to approach the bloggers, and that’s how we built our initial following. So we’ve been very good at spotting trends and tailwinds before anybody else catches on?

Alejandro: Got it. Really, really cool. Why do you think the insurance tech space, as a whole, has exploded literally in the past couple of years? I mean, 10 years ago, 15 years ago, this was unheard of.

Jennifer Fitzgerald: Yeah. Exactly. Even really five years ago. 

Alejandro: Yeah.

Jennifer Fitzgerald: I think the big thing is just timing as most things in life. We saw insurance as the final frontier if you look at all the big verticals in financial services. Insurance was the last one that hadn’t really spawned a digital-first, tech-first-oriented company. You’d seen it in payments. PayPal was the first to breakthrough. You’ve seen it in lending; you’ve seen it in wealth and in banking. Insurance was the final frontier.

Alejandro: In your case, I understand that investors were very impressed with your playbook when it comes to growth. Why is that the case?

Jennifer Fitzgerald: Because it’s hard. Anybody who’s tried to acquire customers in financial services or insurance knows how hard and expensive it is. One stat that I like to talk about is Google AdWords. Anybody can go in and start bidding on AdWords in Google. The most expensive set of AdWords relate to insurance. So I think the thing about our playbook that has investors taking notice is we’ve been able to figure out how to acquire customers in a way that doesn’t make our economics upside-down. We have shown significant growth year over year, like tripling volumes. But our customer acquisition cost, we’ve kept flat, and that’s a dynamic that you hardly ever see. Usually, when you’re scaling aggressively, your acquisition costs go up because you lose advantages and channels; channels get more expensive over time. We’ve shown that we can grow significantly and keep those customer acquisition costs flat.

Alejandro: Any recommendations for the folks that are listening on how to keep the customer acquisition cost flat?

Jennifer Fitzgerald: Sure. A few. One is, especially if you’re a consumer-focused company, channels change all the time. I think three or four years ago, everybody was on Facebook, advertising, and Facebook was the thing. Now, that’s not the case. Costs have gone up significantly on Facebook, and you see a lot of companies retrenching for Facebook because of the cost of acquisition and the shifting demographics. Facebook users are getting older and older. Younger consumers are spending more time and attention elsewhere. The big thing is making sure that you’ve got a marketing team and engine that is nimble and can move into opportunities before anybody else does because there’s no silver bullet. It’s a lot of hand-to-hand combat channels, and as soon as people start to catch on, that arbitrage in that specific channel begins to erode and compress. So you’ve got to move onto the next thing. That’s one piece of it. The second piece of it is, you’ve got to build a brand and a product that solves a customer pain point. We have always just been laser-focused on solving the customer problem, for writing the best customer experience in market. What that has done is, it has generated a lot of organic referrals our way. Up until recently, we haven’t had a paid referral program. Our customers have just referred other people based on the great experience that they had, and that’s generated a significant amount of inbound volume for us that’s “free.”

Alejandro: Got. Also, insurance tech, the market as a whole is massive. So how big is it?

Jennifer Fitzgerald: In terms of premium every year the consumers are spending on insurance, it’s in the hundreds of billions. Home and auto insurance is about 300 billion a year. Life insurance is 150 billion a year. These are big, big markets.

Alejandro: Wow. In your guys’ case and perhaps for the people that are listening, what have been your biggest takeaways on how do you tackle such a big market like this?

Jennifer Fitzgerald: For us, it’s been – and it’s probably applicable to other companies. You’ve got to focus. That means figuring out where the biggest opportunity is that you have a strong right to win. Because when you’re small, you can’t take on everything at once, because I think you’re going to do everything not well. And that’s not going to move the needle. One of the analogies we talk about internally is don’t move 20 footballs one yard. You want to move a handful of footballs to the end zone. So we have just been very, very focused on where we have a strong right to win, proving that out, and then expanding horizontally when we’re ready.

Alejandro: Got it. We were talking about the fundraising earlier, and I just want to follow-up on that. Up until very recently, it has been like this boys’ club that’s complete nonsense, and this comes from a father of three little girls. So I’m very glad that this has been changing, but you have been at it for five or six years now. My question to you is, have you seen a change in this boys’ club mentality, and did you feel a disadvantage at any point?

Jennifer Fitzgerald: I don’t know that I felt disadvantage because I was a woman, because I don’t know what it’s like to not to be a woman. So I don’t have the AB test there. I think being an entrepreneur and founder is hard regardless of your back story. I think what’s made it harder for me is – it’s true regardless I think of being a man or woman is being a first-time founder. I didn’t have a successful startup brand on my resume. So, for example, if I were somebody who came from Airbnb or Facebook, I think raising capital and getting support for my own company would have been easier for man or woman. I think just being a first-time founder who’s not from a successful brand name startup company, it’s just going to be hard. Full-stop. Then coming at it in an industry where very few investors had any experience, which was insurance, is also harder. My parents like to joke that I love to do things the hard way. I just took probably the most difficult possible route into starting a company. With that said, I’ve had good experiences by and large with the VC community. I’ve got an incredible board of investors who are incredibly supportive and have believed in me as the CEO and founder, and then us as a company for the last several years.

Alejandro: Got it. So for the female founders that are listening, what piece of advice would you give them?

Jennifer Fitzgerald: Keep at it. If you’ve got a solution or a product that solves a real market problem, keep at it. Find the folks that will believe in you whether that’s investors, whether that’s employees. But you’ve got to stay persistent. I think one of the things early on that helped is I built a lot of credibility with my work at McKinsey and the relationships that I built on the insurance industry side. That’s something that I could bring to the table that shows, “I’ve been working in this. I’m experienced. I have relationships. I know what I’m talking about. One of the sayings that my dad, who’s ex-military, likes to say is “You’ve got to have your s*** in one sock. As a woman, it doesn’t hurt to have it on one sock. Is it fair that you’ve got to have it in one sock more than the guy next to you? Maybe, but can’t hurt. Right.

Alejandro: Yeah. Absolutely. How big is the company today?

Jennifer Fitzgerald: We are 250 people.

Alejandro: Wow. How did you also grow yourself in parallel with that company growth so that you were not outgrown by the business?

Jennifer Fitzgerald: A great question. It’s something that I am working on every single day because every single day, it’s the biggest company I’ve ever let. I think a few things have helped me along the way. One is, trying to be open to feedback from employees and from our investors. Two, and this is probably the most helpful thing that I’ve done is, building a peer network of CEOs and founders of similar-stage companies or preferably companies a little bit ahead of us, to sanity-check how I’m approaching things, understand what things I’m dealing with are common versus uncommon, trying not to reinvent the wheel on things. It’s been huge, and it’s allowed me to try to change the arch of my own development as a leader and help me scale with the company.

Alejandro: Got it. I guess the industry as a whole, where do you see it going?

Jennifer Fitzgerald: I think there’s going to be a lot more investment. You’re going to see a lot more insurance tech companies over the next few years. I think it is still very much early innings for this space because you still haven’t seen a big breakout company go public or get acquired for a huge exit. So I think it’s still early innings. I think what you’re going to see broadly overall in financial services is consolidation because of how difficult it is to acquire customers. I think that’s why you’re seeing a lot of companies on the fintech side now trying to be the bank. So everybody’s launching their savings product, their checking account, their debit card, their credit card. They might have started just with a budgeting app or maybe investing. So you’re seeing everybody expand horizontally to try to deepen their shared wallet with the customers that they’re already acquiring. So I think consolidation is something that you’re going to naturally see happen over the next five to ten years.

Alejandro: Got it. In your own journey, Jennifer, the journey is tough being a founder. Looking back, what would you say has been your toughest moment, and how did you overcome that moment?

Jennifer Fitzgerald: I think the toughest moments for me were the early days of just a lot of self-doubt, getting told no, not having any strong idea of what I was doing in terms of raising capital, hiring our initial employees. A lot of self-doubt groups, especially if you are of the insecure, overachiever archetype of which I was, and I think a lot of founders are. You’re used to knocking down walls and getting ahead by putting your head down and working harder and smarter than anybody else, but that’s not necessarily the recipe for being a successful founder. You have to have muscles that maybe you’ve never exercised before. A lot of times, it’s on the sales side. Quite frankly, a lot of it boils down to timing and luck. Are you working on the right problem at the right time in the market? A lot of things are out of your control, and I think realizing that a lot of things were out of my control – it was a difficult transition for me, but acknowledging that every day is something that’s gotten easier and easier.

Alejandro: When you’re hearing the word “no” – I’m sure there are a lot of people that right now are thinking, “I’m listening, and I’m hearing the word “no” back and forth. Maybe they are questioning themselves why they’re doing this and if they’re the right people to do this. What words of wisdom would you have right now to share with them?

Jennifer Fitzgerald: I think the big thing when you’re hearing no, no, no is to be able to judiciously figure out what’s valid feedback and things that you should take into account about your approach or your business model, or the product and service that you’re building. Sometimes, the noes are actually based on things that you should take into account. Sometimes, the noes are just arbitrary. Or it’s a timing thing, or somebody had a bad day. It’s almost impossible to be able to distinguish between the two buckets, but it’s absolutely vital that you do because sometimes you’re getting a lot of noes because you are building something that isn’t addressing a real problem. What you built is a solution in search of a problem, and it’s not a fundable idea versus you have built something that is a compelling solution to a real problem in an addressable market, but your pitch isn’t connecting, or you’re talking to the wrong people. Distinguishing between which bucket you fall in is really tough, and I think the only thing that you can continue to do is seek feedback from people that you trust and be open, receptive to the fact that you might be wrong in a few things, and you might need to adjust something about your business or your pitch or your product and service offering in a way that’s going to resonate with the market and with potential investors.

Alejandro: Got it. There’s one question that I always ask the guests that we have here on the show, and that is, knowing what you know now, Jennifer, if you had the opportunity of having a chat with your younger self, with that professional that was still in McKinsey and thinking about making the leap of faith and starting a business, what would be that one piece of business advice that you would give to your younger self and why?

Jennifer Fitzgerald: I would tell my younger self to chill out a little bit and enjoy the journey more. I think especially through my 20s and 30s I was very, very focused on achieving goals, what’s next, kind of listening to the inner anxious voice about, “I have to do more. I have to do it faster.” I think earlier on, I would have benefited more from just enjoying the journey. Still doing the right thing, still taking the right risks, but be a bit more relaxed about it.

Alejandro: For example, now, in your own case, how are you enjoying the journey?

Jennifer Fitzgerald: I take time to see friends, which I didn’t a few years ago. Just basic things like that. Carving out a little bit of time for yourself or realizing that an extra hour of sleep versus an extra hour of work isn’t going to make or break the business at this point. Even like little, little tiny things make a huge difference.

Alejandro: Got it. And just to really wrap it up on Policygenius, in a world where the vision that you have is fully realized, what does that look like?

Jennifer Fitzgerald: That looks like Policygenius being a household name. That looks like people coming to Policygenius to make their insurance and financial shopping product decisions the same way they default go to Amazon for everything else.

Alejandro: Really cool. And for the folks that are listening, Jennifer, what is the best way for them to reach out and say hi?

Jennifer Fitzgerald: Best way to reach out, you can visit us at our website at or I’m on Twitter @jenlfitzgerald. 

Alejandro: Amazing. Well, Jennifer, thank you so much for being on the DealMakers show today.

Jennifer Fitzgerald: Thank you for having me.


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