Pie Insurance business insurance

Overview

Pie Insurance is a technology-driven insurer built around one product: workers' compensation for small businesses. It started in 2017 as a managing general agent and became a full-stack carrier after AM Best rated its insurance companies in February 2023. Its comp policies are written by The Pie Insurance Company (NAIC 21857) and its pooled affiliate, Pie Casualty Insurance Company, which together form Pie Insurance Group. NAIC files them as their own group, Pie Group Holdings.

Pie is independent and privately held. It has raised more than $615 million of venture funding since 2017. At the start of 2026 it reported more than 55,000 policies in force, up more than 25% in a year, and a network of more than 5,000 partner agencies.

Pie also sells business owner's, general liability, commercial auto and professional liability policies. Those are not on Pie's own paper. Pie Insurance Services, Inc., the company's licensed agency, places them with third-party insurers that are not affiliated with Pie. When you buy one of those, you are dealing with Pie as an agent, and the policy is issued by another insurer.

Co-founder John Swigart is CEO. The company describes itself as remote-first and dates its press releases from Washington, D.C.

History

John Swigart and Dax Craig founded Pie in May 2017, aiming to price small business comp more granularly with data and machine learning and to sell it online and through agents. In its first years Pie operated as an MGA, writing on paper from SiriusPoint America Insurance Company. Pie said in 2023 that it was the fastest-growing workers' comp writer in the country by direct written premium growth from 2020 to 2022, a ranking it calculated itself from S&P data.

Key steps since:

• February 2023: AM Best assigned A- (Excellent) ratings to The Pie Insurance Company and Pie Casualty Insurance Company, and Pie moved its book onto its own paper. It also began building an in-house claims team to replace a third-party administrator.
• 2023: Ford Pro Insure, a commercial auto product for Ford fleet customers powered by Pie, launched in Arizona, Illinois and Tennessee.
• March 8, 2024: AM Best placed Pie's ratings under review with negative implications after 2023 results showed material underwriting losses from adverse reserve development in its New York book.
• March 27, 2025: AM Best affirmed the A- ratings with a stable outlook after Pie commuted reserves and returned to profitability in 2024.
• 2025: co-founder Dax Craig announced he was stepping away from his role as president after nearly eight years.
• August 12, 2025: launched workers' comp in Connecticut, reaching 39 states plus D.C.

New York does not appear on Pie's current list of states.

Business insurance products

Workers' compensation. Pie's own product, with statutory workers' comp and employers' liability for small employers. Pie says its pricing gives instant decisions on 73% of class codes. A quote needs your payroll and class codes, and Pie has a tool to help you find the right code. Pie advertises savings of up to 30% compared with what a business pays now. That figure is its own marketing claim, it varies by business, and Pie says the savings do not apply in Wisconsin.

Pay-as-you-go billing. Pie connects to your payroll provider so each monthly premium is based on actual payroll. You pay no upfront deposit and are less likely to get a bill after the year-end premium audit (see pay-as-you-go workers' comp: how it works and who it suits).

Other small business coverage (placed by Pie as an agency). Business owner's policy, general liability, commercial auto, professional liability and E&O are underwritten by unaffiliated insurers. Pie's site does not name those insurers, so ask which company is on the policy before you bind.

Who it insures

Pie targets small businesses across a wide range of class codes, and its releases mention restaurants, construction, retail, healthcare, professional services and manufacturing. It writes comp in 39 states and D.C., and its 2025 release says those states cover about 83% of U.S. small businesses. You cannot buy Pie comp in New York, Massachusetts or the four monopolistic state-fund states (North Dakota, Ohio, Washington and Wyoming), and several smaller states are also missing.

It is built for small accounts. A larger employer looking for a loss-sensitive plan, a large deductible program or multistate coverage outside Pie's footprint will need a different market.

How to buy

There are three ways in:

• Direct: get a workers' comp quote online at pieinsurance.com in about three minutes, or call 855-705-2716, weekdays 9 a.m. to 9 p.m. ET.
• Through an agent: Pie works with more than 5,000 independent agencies, which quote through Pie's partner portal or comparative raters such as Bold Penguin, Tarmika and Appulate via API, and can download policies through Ivans.
• Embedded partners: platforms that offer Pie comp inside their own software.

Policyholders manage their policy, payments and documents through an online account, and can request loss runs and print required workplace posters from the claims page. Commercial auto customers have a separate service line, 800-438-5374.

Claims

Pie asks you to report within 24 hours. File a first report of injury or a commercial auto loss online, by calling the 24/7 intake line at 844-581-0828, or by emailing [email protected] with your business name, policy number, contact details, the injured worker's name and contact information, and the date, state and description of the incident. For an emergency, call 911 first.

After a report, Pie calls to collect details and decides whether the claim is covered. If it is, your claims professional explains benefits and next steps. Pie built an in-house claims organization starting in 2023 and is led by Chief Claims Officer Carla Woodard, formerly of EMPLOYERS. Its workplace safety research and resources aim to help small employers prevent injuries; see reporting a workplace injury: what employers must do for what employers must do after one.

Financial strength and ratings

AM Best affirmed the A- (Excellent) financial strength rating of The Pie Insurance Company and Pie Casualty Insurance Company on March 27, 2025, with a stable outlook, removing the ratings from the review with negative implications that began in March 2024. AM Best assesses Pie's balance sheet as very strong, with risk-adjusted capital at the strongest level at year-end 2024, but rates its operating performance only adequate and its business profile limited. The trigger for the review was adverse reserve development on New York business that produced material 2023 underwriting losses. Pie later commuted those reserves.

Pie is private and does not publish full financial statements. It does not appear in J.D. Power's small commercial study.

Strengths and weaknesses

Pie is a fast, easy comp market for small employers, and it is now a rated carrier with a few years of history. It is also narrow. It owns one line, and its 2023 reserve problem is recent.

• Strengths: Online quotes in minutes and instant decisions on most class codes. Pay-as-you-go billing tied to payroll. Its own A- (Excellent) rated paper for comp, affirmed with a stable outlook in March 2025. Many ways to buy: direct, through more than 5,000 agencies, or through raters and embedded partners.
• Weaknesses: Comp is the only line on its own paper. BOP, GL, auto and professional policies come from unnamed third-party insurers. It writes in 39 states plus D.C., not New York or Massachusetts. AM Best rates its operating performance only adequate and its business profile limited, and it put Pie under review in 2024 after New York reserve losses. Pie is venture-funded and private, so little financial detail is public.

How to contact Pie Insurance