Pie Insurance vs Simply Business

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. ^{2,5,3,7,8,9,10}Company-reported. Current 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. ^4,24,22Verified. Website 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. ^5,25Company-reported. Producer identity and Pie-published US license list; Wisconsin’s regulator separately identifies this entity in a 2024 administrative action.

Simply Business describes its U.S. service as an online commercial-insurance marketplace and licensed producer connecting business customers with insurers. Its June 30, 2026 Terms identify Simply Business, LLC and Harborway Insurance Agency, LLC d/b/a Harborway Insurance as licensed producers, with Harborway a Simply Business subsidiary; the Terms say Harborway policies are underwritten by Spinnaker Insurance Company. Other site policies are underwritten by third-party providers, so the selected issuer depends on the offer and policy. These roles and license statements are company-reported. The contact-page footer says Simply Business, LLC is licensed in all U.S. states and D.C.; for California it says the company operates under the name Simply Business Insurance Agency, LLC and displays License #0M20593. The footer also lists Colorado, New York, Pennsylvania and Texas operating names; it gives no other license identifiers. No regulator lookup was performed or required for this candidate. ^26,27,39,28Company-reported. U.S. commercial insurance distribution described by the company. Simply Business, LLC, Simply Business, Inc., Harborway Insurance Agency, LLC, the stated parent and each policy issuer are distinct. The Inc./LLC relationship remains unresolved.

Small businesses can start a workers’ compensation quote online or through an insurance agent; agencies use a separate partner portal. ^2,1,3Company-reported. Workers’ compensation access for small businesses and agencies; other product pages direct buyers to quote or contact flows but do not document the same process.

Have your ZIP, payroll and class-code details ready for a Pie workers’ compensation quote; its online intake begins with ZIP code. ^6,3Company-reported. Unauthenticated first step and Pie’s description of workers’ compensation quote inputs; no data was entered and the flow was not advanced.

Pie advertises a workers’ compensation quote in about three minutes, but this company estimate does not predict underwriting or binding time. ^3,1Company-reported. Workers’ compensation quote marketing; no timed independent quote test was performed.

The company advertises online quotes and weekday phone access to licensed agents. Its Terms say a quote is not guaranteed and Simply Business cannot bind a risk without panel-member approval; a quote or online purchase path does not establish that every applicant can bind online. ^28,27Company-reported. Published U.S. quote and service channels. Binding depends on panel-member approval and the individual offer.

Pie policyholders can manage payments, download documents and request workers’ comp certificates online; custom certificates may require your agent. ^15,16Company-reported. Published 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. ¹⁹Company-reported. Pie 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. ^16,21Company-reported. Different company-published consumer and agency descriptions of workers’ compensation renewal. Neither guarantees renewal or unchanged terms; the account notice determines the applicable process.

Simply Business lists licensed-agent phone support Monday through Friday: sales 8 a.m.–8 p.m. Eastern Time and service 9 a.m.–6 p.m. These listed hours do not establish a response-time guarantee. ²⁸Company-reported. Hours displayed on the current U.S. contact page; no actual wait-time observation is implied.

The company describes account access for policy documents, certificates, account updates and adding coverage; help material routes some changes to an agent or insurer. Not every policy change is described as self-service. ^28,29,27Company-reported. Company-described post-purchase service paths; available tasks may depend on policy and insurer.

The Help Center FAQ says most customers opt into automatic renewal and gives 60-day notice and 30-day processing timing only for those who opt in. The same Help Center summary and June 30, 2026 Terms use broader automatic-renewal wording without the FAQ’s opt-in qualification. The public descriptions conflict; they do not establish which wording applies to every policy. ^29,27Conflicting sources. Company-published descriptions reviewed 2026-09-29. FAQ detail, Help Center summary and Terms are inconsistent; no buyer-specific policy notice was reviewed.

Report workplace injuries to Pie within 24 hours through its form, phone or email; Pie says a claims professional follows up and assesses coverage and benefits. ²⁰Company-reported. Published first-report process for Pie-serviced workers’ compensation claims; state notice rules and the issuing carrier’s policy still apply.

Ask who handles your state’s workers’ comp claim: Pie says it manages claims in 34 states and CorVel in five, a split not reconciled with its separate 40-state-plus-DC availability. ^21,11,22Conflicting sources. Public allocation of workers’ compensation claim handling; the current handler for an individual policy should be taken from its state kit and claim instructions.

The Terms say third-party insurers underwrite site policies and each provider handles claims on its own policies; the Help Center directs policyholders to identify and contact the insurer. This establishes a published route, not agency assistance after notice or claim outcomes. ^27,29Company-reported. General site-policy claim responsibility. Harborway/Spinnaker applies only to the named Harborway placement relationship.

Small businesses looking for workers’ compensation can approach Pie directly or through local, regional and national agencies. ^2,3Company-reported. US small-business workers’ compensation distribution described on Pie’s current About and product pages.

Simply Business says it serves small businesses and solopreneurs and lists examples such as contractors, cleaning businesses, LLCs and sole proprietors. These examples describe its stated audience, not guaranteed insurer eligibility or availability. ^26,31,27Company-reported. Company-described U.S. audience; eligibility varies by insurer, state and business details.

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. ^17,18Company-reported. Pie’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. ¹⁷Company-reported. Credit-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. ¹⁶Not publicly disclosed. Workers’ 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. ^21,5Not publicly disclosed. Agency-distributed workers’ compensation and other third-party placements; expired promotional incentives were not treated as current standard compensation.

The Terms say Simply Business receives commission or other compensation from or through panel members and that customers may also incur separate processing, administrative, service, installment or cancellation fees. They give no amount or placement-specific applicability; the Terms say charges are disclosed before purchase. ²⁷Company-reported. General disclosure dated 2026-06-30; no specific commission, fee schedule, premium or customer charge was reviewed.