Market Metrics
Valuation
$2B
+145% from May 2020
Total Raised
~$615M
Across 5 rounds + debt facility
In-Force Premium
~$1B
Up from $650M Mar 2022
Profitability
GAAP positive 2026
First insurtech to consistently profit on workers' comp
Updated at 2025-FY
Funding History
Total raised: ~$615M · Latest valuation: $2B
| Round | Date | Amount | Valuation | Key Investors |
|---|---|---|---|---|
| Seed | Jul 2017 | $4M | - | Moxley HoldingsSirius Group |
| Series A | May 2018 | $11M | - | Greycroft (lead)MoxleySirius |
| Series B | Jul 2019 | $45M | - | SiriusPoint (lead)Greycroft |
| Series C | May 2020 | $127M | $815M | Gallatin Point Capital (lead)SVB CapitalGreycroft |
| Series D | Mar 2022 | $315M | $2B | Centerbridge Partners (lead)Allianz X |
| Debt facility | 2024 | $113M | - | KKR (debt) |
Updated at 2025-FY
Product Specifications
| System | Type | Status |
|---|---|---|
| Workers' Comp | API-issued SMB workers' compensation | Production (200K+ policies) |
| Commercial Auto | SMB commercial auto (added 2022) | Production |
| BOP | Business Owner's Policy (added 2024) | Production |
| Pie Casualty | Captive carrier for retained business | Production (2025+) |
Updated at 2025-FY
Partnerships & Investors
SiriusPointInvestor + Capacity
Long-standing capacity provider; A-rated paper backed Pie's earliest policies
Allianz XInvestor
Series D investor; provides European capacity for future expansion
Centerbridge PartnersInvestor
Lead Series D; insurance-services PE specialist
Updated at 2025-FY
Key Milestones
2017
Company Founded
John Swigart (ex-Esurance COO) and Dax Craig launch Pie in DC to digitally underwrite SMB workers' compensation: historically a paper-broker-heavy line
2018
First Policies Bound
Begins issuing workers' comp policies via broker API; pricing in <3 minutes vs incumbent 3-5 day turnaround
2020
100K Policies
Hits 100,000 small-business workers' comp policies in force; backed by Sirius Group A-rated paper
May 2020
Pandemic Resilience
Series C $127M closes despite COVID; workers' comp claims fall industry-wide due to remote work. Pie loss ratio drops to mid-50s
Mar 2022
Unicorn Status
Series D $315M at $2B; Centerbridge + Allianz X co-lead; ~$650M in-force premium
2023
Profitability Approached
Reaches positive contribution margin on core book; expense ratio in low-20s thanks to API-only distribution
Sep 2024
S-1 Filed for IPO
Confidentially files S-1 with SEC; targets early-2025 IPO at $2.5-3B valuation
Q4 2024
IPO Pulled
Withdraws IPO timeline amid insurtech-cohort underperformance; cites '"better to wait for proven public-market appetite"'
2025
Pie Capital + Captive
Launches captive insurance entity Pie Casualty to retain underwriting risk on profitable books; reduces dependence on fronting carriers
Apr 2026
Profitable on Net Income
Reportedly first full year of GAAP net income; ~$1B in-force premium; IPO discussions resume for late-2026
Updated at 2025-FY