John Swigart + Dax Craig found Pie Insurance 2017 in Washington DC as workers' comp insurtech for small businesses (5-200 employees). Raises $4M seed. Bet: traditional WC quote takes 1-2 days via agent; Pie can quote+bind in 3 minutes for SMBs via NAICS data + state filing data + algo pricing.

Pie Insurance Series A Jul 2017 $4M led by Greycroft + Sirius Group. John Swigart + Dax Craig build workers' comp insurtech for SMBs. Bet: small businesses underserved by traditional WC market; algo pricing + 3-minute quote-bind opens segment historically ignored by large carriers.

Pie Insurance binds first workers' comp policy Mar 2018 in 5 states; by Dec 2018 active in 16 states. Sierra Specialty Insurance Co + Accident Fund as carrier capacity providers. Raises $45M Series B Aug 2019 led by SVB Capital. Goes from zero to $100M premium run-rate in 30 months — fastest WC insurtech ramp ever.

Pie Insurance Series C Sep 2020 $127M led by Allianz X + Greycroft + Sirius Group; valuation $475M. Pie active in 30+ states by EOY 2020. Workers' comp insurtech ramping at SMB scale — average policy $1,200 premium vs traditional WC $5K+. Pie quote-to-bind in 3 minutes.

Pie Insurance Series D Sep 2022 $315M led by Centerbridge Partners at $1.5B valuation; one of last unicorn insurtech rounds pre-rerating. CEO John Swigart targets $400M+ premium 2023. Pie's tech-enabled WC quote-bind for SMBs defies insurtech rerating narrative.

Pie Insurance files confidential S-1 IPO Mar 2024 targeting $2B+ valuation; led by John Swigart CEO. Underwriters: Goldman Sachs, JPMorgan. Pie surpasses $400M run-rate premium by 2024 — fastest-growing WC insurtech. IPO subsequently pulled mid-2024 amid insurtech valuation compression (Lemonade, Hippo, Root trading well below IPO).

Pie Insurance withdraws S-1 IPO filing Jun 2024 — Mar 2024 confidential filing pulled mid-year amid insurtech valuation compression. Lemonade, Hippo, Root trading well below IPO. CEO Swigart refocuses on profitability path before refiling 2026.

Pie Insurance Q4 2024 — surpasses $600M premium run-rate; combined ratio 100%. Still pre-IPO after Mar 2024 S-1 was pulled mid-year. John Swigart CEO refocuses on profitability path before refiling IPO 2026. Pie remains fastest-growing US WC insurtech.

Pie Insurance Q4 2025 — surpasses $700M premium run-rate; combined ratio 95%; first profitable quarter. John Swigart CEO. IPO refiled Apr 2026 at $1.8B target valuation (down from 2024 $2B+ target). Pie's tech-enabled WC quote-bind for SMBs differentiates from traditional WC market.