Pie Is Modernizing The Insurance Industry

Insurance is a 600-year old industry that operates like one,” says Pie Insurance co-founder Dax Craig about the business he hopes to revolutionize. Launched in 2017, his insurance technology startup focuses on modernizing the workers’ compensation insurance process for small- to medium-sized businesses. It's grown quickly since its inception, and shows no sign of slowing down anytime soon. The DC-based company now offers insurance solutions in 34 states and has introduced its unique offerings to other independent insurance agencies.

The workers’ compensation market has proven to be lucrative, as Pie saw its written premium grow by 150% in the first quarter of 2020. Even in the economic crisis brought on by COVID-19, insure-tech continues to show strong momentum. One of the reasons Pie stands apart from the competition is its reliance on data analytics opposed to the more conventional human underwriter. According to the founders, their process is more streamlined, digitized, and cost-effective, which keeps them ahead of the curve.

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When Craig and co-founder John Swigart came together to start a new kind of insurance company, they did it with the shared vision for what a customer-centric firm could be. The founders' complementary experiences also contributed to the success of the company -- before Pie, Dax Craig was a serial entrepreneur who grew companies like Valen Analytics into a market leader in the property-casualty insurance sphere. Swigart led direct insurance carrier Esurance to become a top performer until it was bought for over $1 billion by Allstate. While their past successes were far from trivial, they saw something special in Pie.

“We set out to transform the small business insurance experience and create an amazing an enduring company, and that’s exactly what we are doing with Pie,” Craig said. “We attribute our success to our technology and data science-enabled approach to workers’ compensation insurance.”

Craig and Swigart realized they were onto something when they saw quarterly sales surge up 100% quarter-over-quarter five times in a row. The firm went from zero to more than $25 million within the first eighteen months. Pie has raised $188 million over four funding rounds – the most recent being the $127 million led by Aspect Ventures in May 2020. Of that amount, $27 million will go towards running the business, while the remaining $100 million will be used to launch Pie Carrier Holdings. This subsidiary will create and purchase insurance companies that will issue a segment of its insurance policies.

Initially headquartered in Washington DC, the firm started building another home base in Denver, Colorado. The firm moved to its new 4,300 square foot office space in October 2018 to accommodate its rapidly growing staff – currently sitting at over 100 employees.