Pie Insurance is an insurtech that sells workers’ compensation insurance to small businesses across the United States. The company is based in Washington, DC, and built its own underwriting arm after several years as a distributor for other carriers. It now works directly with small business owners and with independent insurance agencies.
Website: pieinsurance.com
Head office: Washington, DC
Founded: 2017
Company type: privately held; full-stack insurance carrier
Business focus: workers’ compensation and small business commercial lines
Regions served: 40 states and Washington, DC
Two co-founders started the company in 2017 with small offices in Denver and Washington, DC. The business began as a managing general agent that priced workers’ comp policies with its own data models rather than standard rating tables. It sold its first policy in 2018 and grew through a series of funding rounds and state-by-state expansions. Key milestones include:
The move from outside-carrier distributor to full-stack underwriter took about six years. Pie has since narrowed its focus, stepping back from commercial auto in 2025 to concentrate capital and resources on workers’ comp.
The company built its business around workers’ compensation and has added a few adjacent lines for the same small business customers. Pie sells policies directly online, through independent agents, and through payroll-provider partners. Core offerings include:
Workers’ comp remains the largest and longest-running line, underwritten directly by Pie Insurance. The business owner’s, general liability, and professional liability policies are underwritten by third-party carriers not affiliated with Pie, giving small businesses a fuller set of coverage without Pie taking on that additional underwriting risk itself.
The insurer positions itself against traditional workers’ comp carriers that price coverage from fixed rating tables. Pie says it uses machine learning models to return instant underwriting decisions on most of the class codes it covers. That approach supports three distribution channels at once: direct sales, agency partnerships, and payroll-provider integrations.
Its 2021 move into underwriting gave Pie Insurance more control over pricing and claims than it had as a pure distributor. The company has kept expanding state by state since then, and its 2025 exit from commercial auto points to a renewed focus on workers’ comp as its main growth driver.
Insurance Business America named Pie a 5-Star California Workers’ Compensation Provider in 2025, an honor based on broker feedback on claims handling, pricing, and service. That same year, Pie’s then director of commercial auto was named to IBA’s Rising Stars list, which recognizes insurance professionals under 40.
The company has also published its own research on small business workplace safety in recent years. Check the news section below for Pie Insurance’s latest updates.
Pie Insurance's John Swigart says solely licensing vendor software solutions inhibits differentiation
New findings show employees and employers differ on certain issues
Coverage is now available to more than 365,000 small businesses in the state
Small businesses face big challenges in risk mitigation
Small business workers reveal their chief concerns
