Pie Insurance
Pie Insurance is an insurtech company founded in 2017 by John Swigart and Dax Craig. It specializes in providing affordable workers’ compensation insurance tailored for small businesses across the United States. The company aims to address the needs of small businesses that have often been overlooked by traditional insurance providers. Pie Insurance offers a streamlined digital experience from quote to claim, making the process straightforward and efficient. In addition to workers’ compensation insurance, Pie Insurance also provides commercial auto insurance through a network of over 1,000 agency partners. This dual distribution model allows for quick client submissions and real-time policy tracking. The company operates in 39 states plus Washington, D.C., and is expanding its coverage area. With nearly 400 employees, Pie Insurance has achieved significant growth, surpassing $100 million in annualized premiums in under four years. It holds an A- Excellent rating from AM Best, reflecting its financial stability and commitment to empowering small businesses.
Work at Pie Insurance in HR or recruiting? Claim this page
Headcount trend
Pie Insurance went from 379 employees in Jul 2023 to 347 in Jun 2025. Jan to Jun 2025: 24 people joined, 21 left.
Headcount data through Jun 2025
Org structure
Headcount by department
Hiring now
See all jobsSalaries at Pie Insurance
All salaries12 salary profiles in the US
Most reported roles
H-1B sponsorship
Funding
- Sep 2022 · Series D · $315M · Centerbridge Partners, Allianz X, White Mountains Insurance Group
- Mar 2021 · Series C · $118M · Allianz X, Acrew Capital, Greycroft
- May 2020 · Series B · $127M · Gallatin Point Capital, Greycroft, SVB Capital
- Mar 2019 · Series B · $45M · Sirius Group, Greycroft Partners LLP, Moxley Holdings
- Aug 2018 · Series A · $11M · Greycroft Partners LLP, Aspect Ventures, Sirius Group
- Oct 2017 · Seed · $5M · Sirius Group, Moxley Holdings, Elefund
Peer reviews
Worked with someone at Pie Insurance?
Anonymous peer reviews on OffTheRecord
Similar companies
Pie Insurance FAQ
How many employees does Pie Insurance have?
Pie Insurance has about 347 employees, up 0.6% over the 3 months to Jun 2025.
Does Pie Insurance sponsor H1B visas?
Yes. Pie Insurance filed 2 H1B (LCA) applications in FY2024, according to the latest U.S. Department of Labor disclosures. Most of them were for Engineering roles.
What is Pie Insurance's revenue per employee?
Pie Insurance makes about $865K in revenue per employee, based on $300M annual revenue and 347 employees.
How much does Pie Insurance pay?
6figr has 12 salary profiles for Pie Insurance in the US, with pay broken down by role, level, gender and ethnicity on the Pie Insurance salaries page. See Pie Insurance salaries
How much funding has Pie Insurance raised?
Pie Insurance has raised $621M in total funding; its latest round was Series D in Sep 2022.
Data from Company Prospectus, DOL LCA disclosures, WARN notices and 6figr salary profiles.