Gallagher vs Pie Insurance: How Do They Compare for Business Insurance?

Startups through global companies can use Gallagher for business insurance, risk-management and benefits consulting, including a dedicated technology practice. ^2,3Company-reportedUS commercial brokerage and technology practice; company descriptions, not an underwriting designation.

Former Woodruff Sawyer clients can continue to access legacy client portals through Gallagher after the transition. ¹Company-reportedFormer-name/history alias only; no separate provider or claim that every acquired legal entity has changed its name.

Confirm the entity on your engagement: Gallagher Small Business names Arthur J. Gallagher Risk Management Services, LLC, while former Woodruff Sawyer accounts should check their own documents. ^5,1Company-reportedEntity disclosure is scoped to the small-business channel; not a group-wide contracting-entity assertion.

Small businesses can buy Pie’s workers’ compensation directly or through agents; affiliated insurers underwrite workers’ comp, while outside insurers provide some other Pie products. ^{15,18,16,20,21,22,23}Company-reportedCurrent public Pie brand and US small-business insurance services; this describes group roles, not a promise that every product is available to every applicant.

If parent-company ownership matters, Pie Group Holdings, Inc. owns the website and is regulator-listed parent of Pie Casualty; AM Best identifies the insurer group as Pie Insurance Group. ^17,37,35VerifiedWebsite ownership and the parent shown for Pie Casualty Insurance Company; no claim about voting control or every intermediate subsidiary.

Pie Insurance Services, Inc. is the producer that sells and administers policies; verify its current license in your state because Pie’s own license page is not regulator confirmation. ^18,38Company-reportedProducer identity and Pie-published US license list; Wisconsin’s regulator separately identifies this entity in a 2024 administrative action.

Ask which insurers will quote your account: Gallagher says it accesses multiple markets and selects potential underwriters based on qualifications and client preferences, but public pages do not name the insurer for a specific startup. ^6,3Company-reportedUS public market-access descriptions; no insurer list or carrier logo treated as guaranteed placement access.

Pie workers’ compensation is written by The Pie Insurance Company and affiliates; AM Best says all business moved to The Pie Insurance Company and Pie Casualty Insurance Company as of January 1, 2024. ^18,35,36,37VerifiedPie’s workers’ compensation program; the actual declarations page controls the issuing insurer for a specific policy and state.

Pie Casualty has an A- (Excellent) financial-strength rating with Stable outlook from AM Best, affirmed April 24, 2026; this is an insurer-strength opinion, not a guarantee your claim will be covered. ³⁵VerifiedPie Casualty Insurance Company and the consolidated Pie Insurance Group rating unit as identified in the disclosure report.

For Pie’s BOP, GL, professional liability or cyber, ask which insurer would issue the policy; Pie says outside partners underwrite these lines but its reviewed pages do not name current partners. ^{18,20,21,22,23}Not publicly disclosedCurrent public BOP, cyber, general-liability and professional-liability/E&O pages; account-specific carrier access was not tested.

California buyers should independently verify authority and product access: Gallagher Small Business publishes license 0D69293 and NPN 19837 for Arthur J. Gallagher Risk Management Services, LLC, but this is company-reported and not proof your risk qualifies. ⁵Company-reportedCompany-published producer identifiers checked 2026-09-16; California regulator record not verified.

Get a proposal that names the California producer, insurer and form for each line; reviewed pages do not establish California eligibility or terms for every listed Gallagher product. ^2,6,5Not found in reviewed sourcesReviewed public sources only; office location, contact availability and US marketing are not coverage eligibility.

Confirm all work locations and class codes before relying on Pie workers’ comp: sources conflict between availability in 40 states plus DC and 39 states plus DC. ^{24,25,14,26,35}Conflicting sourcesPublic workers’ compensation footprint as of 15 September 2026; the state-page selector, document library and other marketing surfaces were not internally consistent.

Ask if Pie’s partner-issued BOP, cyber, GL or professional policy is available in your state; the reviewed pages give no product-state map and Pie’s terms limit availability. ^{20,21,23,22,17}Not publicly disclosedPublic availability for Pie’s partner-carrier products; no quote or contact form was submitted.

Ask which Gallagher tools your engagement includes: Go supports client self-service, Submit tracks submissions and documents, and Verify manages certificates. ²Company-reportedCompany-described technology-practice tools; no logged-in testing or universal account entitlement.

Former Woodruff Sawyer clients can use separate portals for benefits, policies, claims, certificates and auto ID cards; confirm which login serves your account. ¹Company-reportedTransition-page descriptions; no portal functionality tested.

Gallagher describes pre-renewal meetings across finance, HR, operations and risk teams, plus contract review and coverage-gap analysis; agree on the timeline and deliverables for your account. ¹⁰Company-reportedCasualty-practice service description, not a promise for all small-business engagements.

Pie policyholders can manage payments, download documents and request workers’ comp certificates online; custom certificates may require your agent. ^28,29Company-reportedPublished workers’ compensation account tutorial; authenticated features were not accessed or independently tested.

Budget for a workers’ comp premium audit: Pie replaces estimated payroll with actual figures and may request payroll, employee, expense and subcontractor records, which can change your final premium. ³²Company-reportedPie workers’ compensation premium audit process; the page does not quantify any resulting additional charge or refund.

Pie’s consumer FAQ describes a workers’ compensation renewal quote about 30 days before expiry for review and acceptance. Its agency FAQ says previews for policies under $20,000 go to the insured with the agency copied, while previews for policies over $20,000 go to the producer; unless otherwise notified, the deposit is drafted and the renewal issued five days before its effective date. The FAQ does not specify the exact-$20,000 case. Ask which notice and payment process applies to your account. ^29,34Company-reportedDifferent company-published consumer and agency descriptions of workers’ compensation renewal. Neither guarantees renewal or unchanged terms; the account notice determines the applicable process.

Request placement-specific compensation because Gallagher may receive commissions, fees, contingent and supplemental commissions or affiliate/intermediary payments; no startup fee schedule is published. ⁴Company-reportedUS compensation disclosure; no fee-free or uniform commission assumption.

Workers’ comp buyers can choose annual, semiannual, quarterly, monthly or pay-as-you-go plans; pay-as-you-go follows reported payroll without a deposit, while monthly plans require 16.6% upfront and ten payments. ^30,31Company-reportedPie’s current workers’ compensation payment pages; actual availability and policy-specific charges need confirmation in the quote.

Include Pie’s 3% card fee in your quote comparison for eligible new single-state workers’ comp policies, except in Florida, Nebraska, Maryland and Rhode Island; the page does not specify multi-state or renewal fees. ³⁰Company-reportedCredit-card payments for new single-state workers’ compensation policies under the current payment-options page.

Ask the state-specific price before requesting a waiver of subrogation because Pie charges for each specific or blanket waiver but publishes no amount. ²⁹Not publicly disclosedWorkers’ compensation waiver requests through Pie’s published service process.

Ask your agent what commission applies because Pie says partner agents earn commissions on workers’ comp policies, but current pages publish no standard rate. ^34,18Not publicly disclosedAgency-distributed workers’ compensation and other third-party placements; expired promotional incentives were not treated as current standard compensation.