Pie Insurance: Five Years Down and Way More to Go

Earlier this year, 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. We’ve transitioned from a young startup crammed into a small office, to a team of more than 400 team members (we call them Pie-oneers) working across the country. Today, Colorado is home to our largest number of Pie-oneers—over 170—and we have no plans to slow our growth.

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 insurers. 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.

Denver roots

I’m no stranger to entrepreneurship in Denver and while Pie has team members spread out across the country, our origin story starts with me, and of course, Colorado. After I sold my wireless and telematics startup in 2000, I co-founded Valen Analytics, a data and analytics provider to property and casualty insurance carriers. I was frustrated because insurance companies weren’t using Valen’s predictive analytics solutions. My 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, my friend encouraged me to start my own insurance company—using the analytics as intended. While for many, creating an insurance company from scratch may have seemed daunting, for me it sparked an idea for the future. As a serial entrepreneur, I’m energized by building things, so I set forth and started to create my own insurance company.

The early days

I met my co-founder, John Swigart in 2016 and as they say, the rest is history! 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 I lived in Denver, John 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 a website, 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.

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 hundreds of millions in funding, 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 my 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.

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 John 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.

Denver Startup Week

Pie has been involved with Denver Startup Week since 2019 and it’s one of our favorite events of the year. It's always an honor to connect with other founders and startup employees to learn about how they’re innovating and cultivating a community of builders in Denver. At Pie, we love having a large presence in the Denver area. It’s my home, I love all the state has to offer, and I’m inspired by the incredible talent here.

This year we’re excited to be sponsoring the product track at Denver Startup Week and have two amazing panels lined up. Attendees can hear from our team on how to build a high performing and scalable engineering team on Monday, and how to uplevel your leaders to prepare for the future on Tuesday. We’ll also be at the job fair on Wednesday and hope to see you there!

Looking to the future

As my fellow founders know, 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. We’ve grown from a team of two to more than 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 without the amazing people and support we have in Denver. While I can’t predict the future, I am very confident we have a fulfilling and long road ahead here in Colorado.