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.

Insurance Washington, United States Founded 2017 ~346 employees Private · Series D

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Employees
346
+0.9% in the 3 months to Sep 2026
Revenue / employee
$867K
Revenue ~$300M
Total funding
$621M
Last round Series D, Sep 2022
12-month attrition
19.2%
Tech: 17.8%
H1B filings, FY2024
2
Sponsors visas
Open jobs
12
Last 30 days

Headcount trend

Pie Insurance went from 373 employees in Oct 2024 to 346 in Sep 2026. Apr to Sep 2026: 17 people joined, 45 left.

Org structure

Headcount by department

Other120
Finance62
Engineering58
Operations40
Success15
HR14
Sales13
Product10

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

Salaries at Pie Insurance

All salaries

12 salary profiles in the US

Most reported roles

Pay by level, gender and ethnicity

H-1B sponsorship

H-1B Sponsorship Limited
H-1B Filings by Department
Engineering2

Peer reviews

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Pie Insurance FAQ

How many employees does Pie Insurance have?

Pie Insurance has about 346 employees, up 0.9% over the 3 months to Sep 2026.

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 $867K in revenue per employee, based on $300M annual revenue and 346 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.