Meet Pie Insurance

Making workers’ comp as easy as pie for small businesses

We’re transforming a 600-year old industry.

Traditionally, small business owners haven’t loved navigating the complicated world of workers’ compensation. High prices, burdensome processes, and a lack of service have  given small business insurance—and workers’ comp in particular—a bad rap. In fact, our research found that 80% of small businesses overpay for workers’ compensation insurance. 


That’s why we’re here.


Pie Insurance provides workers’ compensation insurance directly to small businesses. We also partner with local, regional, and national insurance agencies to provide coverage to their clients. This way, everybody wins. Small business owners can now save up to 30% in minutes—which means getting workers’ comp coverage really is as easy as pie.

“Shopping for insurance should be simple and accessible, just like other products and services we buy online. America’s small businesses deserve a better workers’ comp insurance experience, as well as the ability to find savings in the process.”

John Swigart, Pie Co-Founder and CEO

Get yourself a piece of the pie.

Check out our careers page, and help us build the future of small business insurance. 

View Open Positions

Featured In

The Best of Both Worlds

Since launch, Pie has brought together experienced investors and a talented leadership team. Each person who joins our mission—to make small business insurance as easy as pie—demonstrates the passion and values that drive our rapid growth. Though “rapid growth” means we’re making major waves, Pie is backed by Sirius Group and led by a team of insurance experts, so our product and processes are rooted in stability and experience.

Financial Strength & Backing

Pie Insurance operates as a managing general agency for Sirius America Insurance Company, a subsidiary of Sirius Group, offering A.M. Best A- rated workers’ compensation insurance. To date, Pie has raised $61 million to fund its innovative approach toward workers’ compensation insurance for small businesses.

Pie combines two elements that really stand out - a unique set of underwriting data and an experienced founder who was instrumental in building an online insurance company that was sold for over a billion dollars.

Ian SigalowPie Insurance Investor and Co-Founder of Greycroft