Pie Insurance
Pie Insurance sells workers' comp coverage to small businesses through a licensed carrier and agent network.
On the record
Checkpoint: Deadline for Pie to raise fresh capital or get acquired before cash pressure forces a down round
The call
Pie built a real licensed insurance business with growing distribution, but it hasn't raised money in years while AI-armed giants close the speed gap it once owned.
Pie Insurance sells workers compensation insurance to small businesses using a mostly digital process. It is hard to copy because Pie holds a real insurance license, has thousands of customers, and built relationships with agencies, but the big insurance companies like The Hartford and Travelers are not blocked from doing the same thing, they just have not tried as hard yet. Right now, artificial intelligence is becoming normal in insurance underwriting (AIG showed this in 2026 with help from other tech firms), which means Pie's speed advantage is disappearing fast. The one thing that matters most: whether Pie can raise new money or get bought by someone bigger in the next six to twelve months, because right now the company is not growing and we do not know if it is actually making money on each policy.
Why
01
AI pressure: AIG generative-AI underwriting built with Anthropic and Palantir. AIG's 2026 AI underwriting can quote small-business workers' comp as fast as Pie, wiping out Pie's speed edge. Could AI do the core job? Only partly.
02
Bigger players: The Hartford, Travelers, and Berkshire Hathaway's biBERK. These carriers have the balance sheets and licenses already, and are catching up on digital quoting for small-business workers' comp. Could a giant copy it? Probably.
03
What protects it. Pie holds actual state insurance licenses, an A-rated carrier status, and 5,000 agency relationships that AI tools alone can't replace.
What would change this call
Pie raises a new priced funding round or is acquired within 6-12 months. Would show fresh capital access rather than capital strain.
AM Best changes Pie's rating from its current Stable outlook. A downgrade would show financial deterioration; reaffirmation shows stability.
Pie publicly discloses its combined ratio or loss ratio. Would reveal whether underwriting is actually profitable at scale.
AM Best changes Pie's rating from its current Stable outlook. A downgrade would show financial deterioration; reaffirmation shows stability.
Pie publicly discloses its combined ratio or loss ratio. Would reveal whether underwriting is actually profitable at scale.
Key numbers
- 55,000+ policies in force, up 25%+ YoY
- No priced funding round since Sept 2022's $315M
- 5,000+ partner agencies, up from 1,000 in 2021
Named risks
- No priced primary funding round since Sept 2022 amid a cold insurtech funding market.
- Undisclosed loss ratio and combined ratio leave underwriting profitability unverified.
- Headcount volatility, down from a 2023 peak of 503 to 402-447 by mid-2026.
- AI-driven incumbents like AIG closing the digital-underwriting speed gap that was Pie's differentiator.
- Expanding state-level NAIC AI model regulation could add compliance costs to Pie's pricing algorithms.
Rivals, as read in July 2026
| Rival | Direction | Evidence |
|---|---|---|
| AIG | losing to | AIG shipped generative-AI underwriting built with Anthropic and Palantir as of 2026-06-25 |
| The Hartford, Travelers | contesting | Incumbents already shipping digital AI quoting products as of 2026-04-24 |
| biBERK (Berkshire Hathaway) | contesting | Direct digital-first workers' comp competitor cited in 2026-05-28 comparisons |
| Next Insurance | losing to | Named top pick among SMB insurtechs in vendor comparison content, 2026-05-28 |
| Coterie Insurance | gaining on | Building small-commercial digital quoting, workers' comp listed as coming soon per 2026-04-06 comparison |
Questions people ask
- Is Pie Insurance profitable?
- Pie Insurance has not disclosed audited financials or a combined/loss ratio. In May 2023 it laid off 63 to 66 employees, about 14% of staff, explicitly to reach profitability without new capital, signaling it was not yet profitable at that time.
- Has Pie Insurance had layoffs?
- Yes. In May 2023, Pie Insurance cut 63 to 66 employees, roughly 14% of its workforce, citing a deteriorating funding environment and a push toward profitability without raising new capital.
- Could AI replace Pie Insurance?
- Unlikely to fully replace it: Pie holds a licensed carrier status (NAIC 21857) and an A- AM Best rating that pure software cannot replicate. But AI-driven quoting from rivals like AIG (with Anthropic and Palantir, 2026) is eroding Pie's speed edge.
- Who owns Pie Insurance and is it publicly traded?
- Pie Insurance is privately held and venture-backed, not publicly traded. Its last confirmed priced round was a $315M Series D in September 2022 led by Centerbridge Partners and Allianz X, with no new large primary round confirmed since.
- Who is Pie Insurance's biggest competitor?
- Next Insurance is frequently cited as the top pick among SMB insurtechs in 2026 comparison content, while incumbents like The Hartford, Travelers, and Berkshire Hathaway's biBERK also compete directly in digital small-business workers' comp.
- What is Pie Insurance's AM Best rating?
- Pie Insurance's carrier, The Pie Insurance Company (NAIC 21857), holds an A- (Excellent) financial strength rating from AM Best with a Stable Outlook, reaffirmed as of January 13, 2026.
Timeline
- 2026-01-13Reports 55,000+ policies in force, AM Best A- rating reaffirmed with Stable Outlook
- 2025-08Expanded workers' comp coverage to Connecticut, reaching 39 states plus D.C.
- 2023-05-21Laid off 63 to 66 employees, about 14% of staff, to reach profitability without new capital
- 2022-09-25Closed $315M Series D led by Centerbridge Partners and Allianz X, largest US P&C insurtech round of 2022
- 2021-03Closed $118M Series C led by Allianz X and Acrew Capital
- 2020-05Closed $127M Series B led by Gallatin Point Capital
- 2018Closed $11M Series A with Greycroft, Elefund, Aspect Ventures, Sirius Group, Moxley Holdings
- 2017Pie Insurance founded in Washington, D.C.
Revision history
23 July 2026
First assessed. Losing its protection. The text above is fixed as of this date and is not edited afterwards.
In the same band
Sources
- Invest In Pie Insurance Stock (2026-01-13)
- How Much Did They Raise & Key Investors (2022-09-20)
- Pie Insurance completes $118 million funding round (2021-03-26)
- Allianz X leads $118 million funding round of U.S. insurtech Pie Insurance (2023-11-01)
- Pie Insurance Announces $315 Million Series D Round of Funding (2022-09-25)
- Pie Insurance's AI-First Workers Comp Underwriting: A 2026 Case Study (2026-05-06)
- Valuation, Funding Rounds & Stock Price (2025-10-12)
- Revenue, Competitors, Alternatives (2022-04-18)
- Pie Insurance Reports Strong 2025 With Geographic Expansion... (2026-01-13)
- A Message from Pie's CEO
- Pie Insurance Services Number of Employees 2026 (2026-06-29)
- Pie Insurance lays off 14% of workforce amid deteriorating funding environment (2023-05-21)