Jennifer Fitzgerald has raised tens of millions of dollars for her Insurtech startup. They are taking on a space worth hundreds of billions of dollars a year. While she is now seen as one of the first pioneers of this space, it hasn’t always been an easy flight with clear skies. 

I recently caught up with Jennifer on the Dealmakers Podcast to find out more about her journey with her startup Policygenius. She shared her lightbulb moment, the steps to quitting her job for her and her co-founder, Francois de Lame, the fun of fundraising, the advice she wishes she had when she started and how to scale as a leader in a fast-growth company.

Listen to the full audio and for all the details with the transcript here.

Pioneering On The Final Frontier Of Fintech

Jennifer was born in the Philippines. A military brat, with a father in the Air Force, this entrepreneur spent most of her early years jetting around the world for short stints in new locations. 

She’s lived on Air Force bases from Texas to Mississippi, did high school in Virginia, and college in Florida. Then went on to get her law degree, which landed her in New York. 

Little did she realize at the time, but this was all great prep for becoming an entrepreneur and CEO. It taught her to be resilient, to quickly adapt to new situations, to be good at meeting people and being confident in herself in new places. 

Jennifer counts joining the Peace Corps as her first real entrepreneurial experience. She was dropped into western Honduras and tasked with working with locals on finding the most impactful projects to work on for two years. 

She ended up helping local government haul their systems online. An experience that seeded the crazy idea of going into tech. 

Still, she took a detour to go work with the World Bank. She found a very big bureaucracy, which takes many months to get something done, approved and implemented.

That drove her to the private sector, for the hope of being able to move with greater speed and impact, and on a larger scale. 

Discovering the Insurance Space

As I’ve seen many successful founders do, Fitzgerald did a stint in consulting at McKinsey. 

There she gained a really high-level view of business, got a taste of strategy and operations, distribution and insight into multiple industries in a very short period of time. 

This introduced her to the insurance industry. She was tasked with helping very big companies cut costs in the pit of the financial crisis. 

Jennifer and her cofounder saw that insurance in America was still predominantly about local offline insurance agents. They saw the potential for something new, and landed on the initial idea for their startup, Policygenius

Testing Startup Ideas

Before quitting their jobs and going all in, the cofounders set about testing and nurturing their business idea.

The first question being whether something like this already existed. Then they researched, looked at models in different industries, went out to get feedback and had a lot of conversations. 

Then they went all-in with an online insurance marketplace, that would become like the Amazon or Expedia of products in this space. 

While Jennifer says they admittedly may have spent too much time on their first pitch deck, one of their best moves was making their first hires. That included a product designer, head of engineering and content producer, all in the first month. 

They knew investing in content and SEO early would pay great dividends. They didn’t want to be stuck on Facebook or Google Ads. That move paid off well. As has being one of the first insurance companies to really engage on blogs and through podcasting.

Fundraising

Policygenius began by bootstrapping for a while. Yet, they are in a highly regulated and complex industry. Every state has its own rules, even individual zip codes can differ in pricing and policy structure. That makes it a capital intensive business. 

The co-founders spent the first couple of years on the phones themselves, selling and providing customer service. Then they tried to raise a seed round. They went through dozens of pitches, and the VCs and seed level funds just didn’t get it yet. 

So, they got scrappy and raised almost $750k from 50 individual investors. They stretched that capital out for close to two years before raising their Series A round. 

They now have 250 employees and have raised $50 million. Including from top investors like Norwest Venture Partners, Revolution, Susa Ventures, AXA Venture Partners, Otter Rock Capital, and Karlin Ventures to name a few. 

Storytelling is everything which is something that Jennifer was able to master. Being able to capture the essence of what you are doing in 15 to 20 slides is the key. For a winning deck, take a look at the pitch deck template created by Silicon Valley legend, Peter Thiel (see it here) where the most critical slides are highlighted. Moreover, I also provided a commentary on a pitch deck from an Uber competitor that has raised over $400M (see it here).

How to Scale with Your Company as a Leader

Fast growth startups like this mean that founders have to learn how to grow incredibly quickly as leaders too. If you can’t, your business will outgrow you. 

Jennifer’s three top moves for growing as a leader in this respect are:

  1. Making sure you are working on this growth every single day
  2. Staying open to feedback from investors and your team
  3. Building a peer network of CEOs and other startup founders 

Listen to the full podcast episode to find out more, including:

  • 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

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