About Pie Insurance

“We’re building a company that allows small business owners to purchase workers’ comp insurance easily through Pie’s straightforward online process so they can quickly move on with their day.” – John Swigart, CEO

A workers’ compensation provider built for small businesses

Pie Insurance provides workers’ comp coverage to small businesses through a simple online experience. Offering A.M. Best A rated insurance, we leverage data analytics, easy-to-use online features, and a seasoned team of insurance experts to revolutionize workers’ comp for small businesses. Since Pie’s inception, thousands of small businesses have used our online quoting engine, often seeing savings of more than $1,000 a year. 

Pie began selling workers comp insurance policies direct to customers in 2018. Investors include Sirius Group, a global specialty insurer and reinsurer; Greycroft; Aspect Ventures; Moxley Holdings, an early stage venture capital firm for data-enabled businesses; and Elefund, an early stage venture firm with seed investments in fintech businesses. The Sirius Group provides strong insurance backing with $2.5 billion of A rated insurance premium capacity.

Digitizing the insurance experience

As a technology-enabled company, Pie Insurance leverages extensive, high-quality data sets to segment and price small business policies, accurately assessing risks and passing savings on to small business owners. Our approach to selling workers’ compensation insurance addresses a significant pain point for small business owners, who often face a time-consuming and opaque process. 



The Pie team is led by Co-Founder and CEO John Swigart, who has a long history of success in tech-enabled insurance and financial services businesses. Prior to Pie, John served on the Esurance executive team for 13 years, where he initially led all the financial functions and then became the company’s first chief marketing officer. John and his leadership team bring to Pie more than 50 years of insurance industry experience.



“We had a clear but aggressive goal for Pie: stand up a complete insurance operation in under 12 months,” Swigart said. “Within 11 months, Pie’s seasoned team of insurance experts effectively navigated state regulatory environments and surpassed our goal, and we’ll continue to expand rapidly.”



Today, Pie Insurance provides small business coverage in Arizona, ArkansasCalifornia, Colorado, Georgia,  IowaIllinois, Kansas, KentuckyLouisiana, MarylandMichigan, Nebraska, New MexicoNew YorkNorth Carolina, Oklahoma, Pennsylvania, Tennessee, and Texas.



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Awards and Press

2018 Innovation in Action Winner

Strategy Meets Action (SMA), a leading insurance strategic advisory firm, recognized Pie Insurance as a winner of the SMA Innovation in Action Awards. "Our annual awards program gives SMA the opportunity to recognize and celebrate true innovation within the insurance industry,” said Karen Furtado, SMA Partner.

Innovation in Action Award

2018 DC INNO’s “50 on Fire” Winner

Pie Insurance has been recognized by DC INNO's "50 on Fire," a collection of people, companies, and organizations heating up D.C.’s innovation economy.

50 on Fire award

2018 InsurTech 100 Winner

Pie Insurance was recognized for our innovative use of technology to make it easier for small businesses to get workers' comp insurance online. The InsurTech 100 list outlines the innovative technology solutions which are redefining the sector and every leader in the insurance industry needs to know about in 2019.

InsurTech100 Award

How We Help Small Businesses

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