Gallagher vs Pie Insurance

Gallagher arranges business insurance and provides risk-management and employee-benefits consulting. Its technology practice serves startups through global enterprises. ^2,3

Woodruff Sawyer is now part of Gallagher. Gallagher’s transition page retains access to Woodruff Sawyer client portals. ¹

Gallagher Small Business identifies Arthur J. Gallagher Risk Management Services, LLC as its insurance-brokerage service provider. The exact producer for a former Woodruff Sawyer account should be confirmed in the engagement documents. ^5,1

Pie Insurance is a small-business commercial insurance group whose producer, Pie Insurance Services, sells and administers policies. Its affiliated carriers write workers’ compensation, while selected other products are offered through outside carrier partners. ^{15,18,16,20,21,22,23}

Pie Group Holdings, Inc. owns the public website and is the regulator-listed parent of Pie Casualty Insurance Company. AM Best identifies the rated carrier group as Pie Insurance Group. ^17,37,35

Pie identifies Pie Insurance Services, Inc. as the licensed producer that sells and administers policies; its legal page publishes state licenses but is not a substitute for a current regulator lookup in the buyer’s state. ^18,38

Gallagher describes access to multiple insurance markets. Its executive-risk practice says it considers carrier qualifications and client preferences when selecting potential underwriters; these pages do not identify the insurer that would write a specific startup’s policy. ^6,3

Pie says workers’ compensation is underwritten by The Pie Insurance Company (NAIC 21857) and affiliates. AM Best says Pie began writing all of that business through The Pie Insurance Company and Pie Casualty Insurance Company (NAIC 10997) on January 1, 2024. ^18,35,36,37

AM Best affirmed Pie Casualty Insurance Company’s pooled A- (Excellent) financial strength rating with a Stable outlook, effective April 24, 2026. A rating is an opinion of insurer financial strength, not a guarantee that a claim is covered or paid. ³⁵

Pie says business owner’s, general liability and professional liability policies are underwritten by unaffiliated third-party insurers, and its cyber page refers to carrier partners. The reviewed public pages do not name the currently participating insurers for these products. ^{18,20,21,22,23}

Gallagher Small Business publishes California license number 0D69293 and National Producer Number 19837 for Arthur J. Gallagher Risk Management Services, LLC. This is a company disclosure, not an independently verified license or confirmation that a particular California risk is eligible. ⁵

The reviewed technology, small-business product and producer pages do not establish a California-specific insurer, policy form or eligibility rule for each listed product. Obtain a quote identifying the producer and California placement route. ^2,6,5

Pie’s dedicated state page and AM Best describe workers’ compensation in 40 states and Washington, D.C., but Pie’s homepage and January 2026 release say 39 states plus D.C. Confirm the business locations and class codes in the current quote or agent portal. ^{24,25,14,26,35}

The reviewed BOP, cyber, general-liability and professional-liability pages do not publish a product-by-state availability table. Pie’s terms also say products are not available in every US area or situation. ^{20,21,23,22,17}

Gallagher describes Go for client information and self-service, Submit for submission tracking and documents, and Verify for certificate management. Confirm which tools and service team your engagement includes. ²

For former Woodruff Sawyer clients, Gallagher links WS Connect for benefits and documents, Woodruff360 for policies, claim submission and certificates, and CSR 24 for certificates and auto ID cards. ¹

Gallagher’s casualty practice describes pre-renewal meetings involving finance, HR, operations and risk-management stakeholders, alongside contract reviews and coverage-gap analysis. Confirm the renewal timetable and deliverables for your account. ¹⁰

Pie’s policyholder account tutorial describes payment-method updates, instant or custom workers’ compensation certificates, policy details and downloads for policies, state posters, certificates and endorsements. Agent-served customers may need their agent for a custom certificate. ^28,29

Pie requires an annual workers’ compensation premium audit that replaces estimated payroll with actual payroll information. Its audit partner may request payroll and employee records, cash-expense details and subcontractor certificates, so the final premium can differ from the initial estimate. ³²

Pie says it sends a workers’ compensation renewal quote about 30 days before the current term ends for the policyholder’s review and acceptance. ²⁹

Gallagher discloses brokerage commissions or fees, sometimes both, as well as possible contingent and supplemental commissions. Affiliates or other intermediaries may also earn compensation. It directs clients to their representative for placement-specific details; the disclosure provides no startup fee schedule. ⁴

Published workers’ compensation options include annual, semi-annual, quarterly and monthly schedules, plus pay-as-you-go. The monthly schedule requires 16.6% upfront followed by ten monthly payments; pay-as-you-go uses reported payroll and no initial deposit. ^30,31

Pie publishes a 3% credit-card convenience fee for new, single-state workers’ compensation policies, except in Florida, Nebraska, Maryland and Rhode Island. Its page does not describe this fee for multi-state or renewal policies. ³⁰

Pie says each specific or blanket waiver-of-subrogation request carries a charge set by state rules and disclosed individually; the public FAQ does not give a dollar schedule. ²⁹

Pie says partner agents receive commissions on new and renewal workers’ compensation policies, and its legal footer says compensation rates can vary among insurers. The reviewed current pages do not publish the standard rate or the amount attached to a buyer’s policy. ^34,18