Pie Insurance

Pie Insurance is a Washington, DC-based AI-native insurance carrier for US small commercial. Founded in 2017 by Dax Craig and John Swigart (CEO), Pie writes workers' compensation as its primary line and distributes almost exclusively through independent agents. The core product pitch is that a small-business owner — a restaurant, a landscaper, a contractor — can get a bindable workers' comp quote in minutes rather than days, priced by Pie's own underwriting models rather than a legacy class-rating table.

What Pie actually is. Pie is a licensed carrier with its own paper, not a piece of underwriting software a third-party carrier can buy. Between 2017 and early 2023 Pie operated as a managing general agent on SiriusPoint America Insurance Company paper. In February 2023 Pie completed the transition to a rated, full-stack carrier: it had acquired a regional insurer through Pie Carrier Holdings (backed by Gallatin Point Capital and Sirius), renamed the entity The Pie Insurance Company, and secured an A- (Excellent) Financial Strength Rating from AM Best. AM Best affirmed the A- rating with a Stable Outlook at the 2025 year-end update. A reader shopping for an underwriting workstation should treat Pie like Coalition or Shepherd — it is a risk carrier whose AI lives inside its own book, not a vendor product.

Funding and capital structure. Cumulative disclosed equity funding is approximately $615 million across seven rounds. The $315 million Series D closed in September 2022, co-led by Centerbridge Partners and Allianz X with White Mountains Insurance Group joining as a new investor and existing backers (Gallatin Point Capital, Greycroft, Acrew Capital) following. At the time it was the largest US P&C insurtech financing of 2022. Prior rounds include a $118 million Series C (March 2021, led by Gallatin Point) and a $127 million round in 2020 that seeded the carrier-acquisition vehicle. No later round has been publicly disclosed.

Capacity and partnerships. Sirius / SiriusPoint is the key capital and capacity relationship: SiriusPoint invested directly in Pie Carrier Holdings and continues to provide reinsurance capacity behind The Pie Insurance Company. On the distribution side, Pie launched Ford Pro Insure in December 2022 as a Ford Motor Credit-branded commercial auto product powered by Pie — that partnership is winding down, with Pie stopping new commercial auto submissions from 1 December 2025 and issuing no new or renewal policies effective 1 January 2026 or later. Pie publicly framed the split as a refocus on workers' comp.

What the AI does. Pie's proprietary technology underwrites and prices workers' comp risk from structured small-business application data, classifying exposure and generating bindable quotes through the agent-facing portal without a human underwriter in the base flow. In its 2025 year-end update Pie described continued investment in "AI and advanced analytics to improve underwriting speed, pricing precision, and operational efficiency" — consistent with its founding pitch that workers' comp rating for Main Street small business is structurally mispriced by legacy carriers and tractable for a data-native incumbent.

Traction. At 2025 year-end Pie reported 55,000+ policies in force (>25% YoY growth), workers' comp availability in 39 states plus DC, and a partner network of 5,000+ independent agencies. Serving approximately 50,000 small-business customers places Pie in the top tier of US workers' comp insurtechs by policy count.

Analyst gap. No Gartner, Celent, Forrester or Novarica coverage surfaces in public search. Sourcing is trade press (Insurance Journal, Reinsurance News, Carrier Management, Coverager, TechCrunch), Crunchbase reports and Pie's own announcements.