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Celebrating Five Years
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Celebrating 5 Years of Progress, Puns, Partners, and Pie-oneers

Join us in reminiscing about how Pie has grown over the past five years!
Celebrating 5 Years of Progress, Puns, Partners, and Pie-oneers

Pie’s five year birthday

John Swigart

Earlier this week, May 8, Pie Insurance celebrated our fifth birthday. On day one, back in 2017, our work was measured day-to-day—not in months or years. We weren’t even considering this five-year milestone in those early days. Yet, here we are. We’ve transitioned from a young startup crammed into a small office in Washington, D.C. (and occasionally meeting in a Panera in Denver) to a team of nearly 400 Pie-oneers working across the country. 

From the very beginning, Pie was created to serve small businesses. We saw a gap in the insurance market that left small businesses consistently overlooked and overcharged by traditional insurance companies. We wanted to build an insurance company that would live and breathe our mission of empowering small businesses to thrive by making commercial insurance affordable and as easy as pie. Over the past five years, we’ve continued to stand by our commitment, and weigh every decision in light of what’s in the best interest of our small business customers and the insurance agents who serve them.

Pie’s origin

For those who don’t know our origin story, it starts with my co-founder, Dax Craig, back in 2011. At the time, Dax was CEO of Valen Analytics, a data and analytics provider to property and casualty insurance carriers. He was frustrated because insurance companies weren’t buying Valen’s predictive analytics solutions. Dax’s lightbulb moment came during a conversation with a close friend and advisor who incidentally went through a similar situation in the consumer credit industry. Rather than trying to convince others to use the analytics appropriately, Dax’s advisor encouraged him to start his own insurance company—using the analytics as intended. While for many, creating a company from scratch may have seemed daunting, for Dax it sparked an idea for the future. A serial entrepreneur who’s energized by building things, Dax set the idea aside and began thinking about how to go about building an insurance company. 

Dax kept building Valen but had the idea for Pie tucked away until he and I were connected through common investors. I’d spent more than a decade at Esurance building one of the earliest versions of an insurtech and was hungry for my next venture. I’d never built my own business and don’t like jumping into things without a clear path to success. Yet, after many conversations with Dax, we realized the opportunity sitting in front of us, and we made the easiest decision of our working lives to start Pie.

The early days

The early days of Pie were an adventure. From the beginning, we decided to have two company headquarters and hire talent in both locations because Dax lived in Denver, I lived in Washington D.C, and neither of us wanted to move. Our tiny, one-room offices filled up quickly with a handful of Pie-oneers across insurance, engineering, product, HR, and marketing. We built the business using whiteboards and spreadsheets. It wasn’t pretty! In addition to getting to work on branding, values, and putting a website together, we became singularly focused on launching our first workers’ comp product. Once we could show we had a viable insurance solution, we raised a $5 million seed round in October 2017, only five months after we were founded. As Dax puts it, it was a boiler-room-like atmosphere at the time—we worked long hours, and there were stacks of energy drinks to prove it. 

That hard work quickly proved its value when we sold our first policy in March of 2018 and just a few months later, signed our first partner—both of whom, I’m proud to say, are still with Pie today.

Growing and changing

We’ve matured significantly since those seed-funded days, having now raised more than $300 million, and built a world-class team to serve our growing base of customers. The vision for Pie remains the same as when it was just an idea in the back of Dax’s head: use data to create a better insurance product. A better insurance product that meets small business owners where they are, whether that be direct, through a trusted insurance agent, or through their payroll provider. 

Data and analytics drive our business forward and are key to our mission of enabling small businesses to thrive. Today, small businesses and the insurance agents who serve them can get a quote for workers’ comp in minutes, with savings of up to 30%. By starting with workers’ comp, Pie selected an area of the commercial insurance market ripe for disruption. We didn’t have to buy our way into the market—by messing with our unit economics—the way other startups have. By having a better product that could be responsibly sold at a lower price, we were able to convince small business owners and independent insurance agents to try something new.

But as Dax says, analytics and market opportunity alone aren’t enough to run a business and be successful long term. Everything else we’ve built is vital, including, maybe most importantly, our culture. The thing I’m most proud of is the way Pie-oneers show up for each other, our partners, and our small business customers. I tell our team all the time that the culture is so great because it’s not myself or Dax that’s actually doing the hard work to build a culture and foster it. It’s the Pie-oneers who’ve taken ownership of it and made it what it is today. From onboarding sessions with Pie-Pals, to our volunteer Culture Ambassadors who promote DE&I, mentorship, and wellness activities, our Pie-oneers have created a workplace they enjoy, whether they work from home or in the office.

Together, we created a place where people wanted to work, and Pie-oneers pay it forward by serving our customers and partners with best-in-class service. It’s no wonder we regularly see five-star Trustpilot reviews from our policyholders sharing the wonderful experience they had on their annual audit—an experience many of our peers in insurance can only dream of. Our partners have also played a huge role in our success. Without them, Pie wouldn’t be one of the fastest growing insurtechs in the United States.They’ve pushed us to think bigger, to find new solutions, and implement new features to enable them to serve even more small businesses.

Looking to the future

Five years can feel long when you’re solving complex challenges, but looking back, it has gone by in a flash. The road ahead is long, but filled with exciting opportunities. When I take a moment to think about where we’re going, I think about how manual and complicated things were in the past and wonder what the future will look like for Pie. Today we use intelligent, automated systems that make us efficient and effective. I’m excited to see how our next even more technical solutions will make us unstoppable.

If you ask Dax, he’ll tell you his dream is to see Pie become a verb—like so many successful companies before us. You know your company has made it when your name becomes a verb and there’s definitely room for a commercial insurance company to be verb-ified. What do you think? Can we make “You gotta Pie it,” a household phrase? 

We’re taking this birthday week to celebrate all our wins and how far we’ve come. There is no slowing us down. We’ve grown from a team of two to nearly 400. We sold our first policy in March 2018 and now we’re selling tens of thousands of policies every year. We onboarded one insurance agency partner in 2018 and today we work with thousands of partners. We couldn’t do it alone—thank you to our partners, customers, and fellow Pie-oneers who believe in a better way of doing business. Cheers to another great five years ahead.