---
title: "Pie Insurance vs Simply Business"
description: "Compare Pie Insurance and Simply Business by coverage fit, application route, insurer roles and the questions to ask before choosing a small-business policy."
canonical: "https://spot.insure/compare/pie-insurance-vs-simply-business"
page-type: "provider-comparison"
updated-at: "2026-09-30"
---

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[Human-readable page](https://spot.insure/compare/pie-insurance-vs-simply-business)

# Pie Insurance vs Simply Business

Compare Pie Insurance and Simply Business by coverage fit, application route, insurer roles and the questions to ask before choosing a small-business policy.

## Before You Quote

Ask each provider about eligibility, the issuing insurer, policy wording, limits, retentions, exclusions and costs for your business.

## Highlights

Consider Pie Insurance if your business fits small businesses, and Simply Business if it fits small businesses. Their catalogues overlap on business owners’ policy, cyber, general liability; compare each quote route, identified insurer and policy form before choosing. [3](https://www.pieinsurance.com/workers-comp "Workers’ Comp Insurance For Small Businesses") [26](https://www.simplybusiness.com/about-us/ "Our Small Business Insurance Story")

## Provider Reliability Assessments

These sourced assessments are shown for context; this comparison does not select a winner.

### Pie Insurance

Role: Hybrid role.

Broker Spot Score: **5.3/10** (partial score; 45% of this role's weighting included). Assessed 2026-09-23; review due 2026-10-23. Excluded factors: Carrier-Network Strength (The reviewed evidence does not name the carrier and capacity arrangements behind the assessed programs, so the relationships cannot be assessed.); Regulatory Conduct (A complete, exact-entity regulatory-conduct review for the preceding five years is unavailable.).

Carrier & MGA Spot Score: **6.3/10** (partial score; 25% of this role's weighting included). Assessed 2026-09-23; review due 2026-10-23. Excluded factors: Financial Resilience (AM Best rates Pie Casualty Insurance Company A- (Excellent) with a stable outlook, but no reviewed source maps that insurer to a Pie product, and the Missouri figures for The Pie Insurance Company cover one state and one line. The issuing entity’s own resources for the assessed scope are not established.); Claims and Servicing (The evidence does not sufficiently establish responsibility, access and escalation across the assessed services.); Carrier-Network Strength (The reviewed evidence does not name the carrier and capacity arrangements behind the assessed programs, so the relationships cannot be assessed.); Regulatory Conduct (A complete, exact-entity regulatory-conduct review for the preceding five years is unavailable.).

Read the [full reliability assessment](https://spot.insure/insurance-providers/pie-insurance/reliability).

### Simply Business

Role: Broker.

Broker Spot Score: **No Spot Score**. Assessed 2026-09-29; review due 2026-10-29. Excluded factors: Identity and Authority (No numerical score was produced because the overall evidence outcome was conflicting-evidence; excluded factors cannot hide that outcome. Canonical evidence gaps: The relation between Simply Business, Inc. and Simply Business, LLC remains unresolved in reviewed disclosures.; No line/state carrier appointment list, material binding authority evidence, capacity agreement or placement share was reviewed.; The renewal wording conflict remains unresolved; the applicable rule for any particular policy is unknown.; For the all-states-and-D.C. company statement and the other listed state names, the contact page supplies no jurisdiction-specific identifiers or license classes; those details remain unknown.; No state DOI or NIPR producer lookup was run; the CA licence 0M20593 and 'all states' claim are company-reported only.; No carrier-by-state appointment list, and no rating for individual panel carriers, was found.; The Travelers AM Best rating found is for 'Travelers Casualty and Surety Company of America'; the Terms name a differently worded entity, and it is a parent rating, not a broker measure.; UK operations and FCA status were out of scope.); Carrier-Network Strength (No numerical score was produced because the overall evidence outcome was conflicting-evidence; excluded factors cannot hide that outcome. Canonical evidence gaps: The relation between Simply Business, Inc. and Simply Business, LLC remains unresolved in reviewed disclosures.; No line/state carrier appointment list, material binding authority evidence, capacity agreement or placement share was reviewed.; The renewal wording conflict remains unresolved; the applicable rule for any particular policy is unknown.; For the all-states-and-D.C. company statement and the other listed state names, the contact page supplies no jurisdiction-specific identifiers or license classes; those details remain unknown.; No state DOI or NIPR producer lookup was run; the CA licence 0M20593 and 'all states' claim are company-reported only.; No carrier-by-state appointment list, and no rating for individual panel carriers, was found.; The Travelers AM Best rating found is for 'Travelers Casualty and Surety Company of America'; the Terms name a differently worded entity, and it is a parent rating, not a broker measure.; UK operations and FCA status were out of scope.); Regulatory Conduct (No numerical score was produced because the overall evidence outcome was conflicting-evidence; excluded factors cannot hide that outcome. Canonical evidence gaps: The relation between Simply Business, Inc. and Simply Business, LLC remains unresolved in reviewed disclosures.; No line/state carrier appointment list, material binding authority evidence, capacity agreement or placement share was reviewed.; The renewal wording conflict remains unresolved; the applicable rule for any particular policy is unknown.; For the all-states-and-D.C. company statement and the other listed state names, the contact page supplies no jurisdiction-specific identifiers or license classes; those details remain unknown.; No state DOI or NIPR producer lookup was run; the CA licence 0M20593 and 'all states' claim are company-reported only.; No carrier-by-state appointment list, and no rating for individual panel carriers, was found.; The Travelers AM Best rating found is for 'Travelers Casualty and Surety Company of America'; the Terms name a differently worded entity, and it is a parent rating, not a broker measure.; UK operations and FCA status were out of scope.); Disclosure Clarity (No numerical score was produced because the overall evidence outcome was conflicting-evidence; excluded factors cannot hide that outcome. Canonical evidence gaps: The relation between Simply Business, Inc. and Simply Business, LLC remains unresolved in reviewed disclosures.; No line/state carrier appointment list, material binding authority evidence, capacity agreement or placement share was reviewed.; The renewal wording conflict remains unresolved; the applicable rule for any particular policy is unknown.; For the all-states-and-D.C. company statement and the other listed state names, the contact page supplies no jurisdiction-specific identifiers or license classes; those details remain unknown.; No state DOI or NIPR producer lookup was run; the CA licence 0M20593 and 'all states' claim are company-reported only.; No carrier-by-state appointment list, and no rating for individual panel carriers, was found.; The Travelers AM Best rating found is for 'Travelers Casualty and Surety Company of America'; the Terms name a differently worded entity, and it is a parent rating, not a broker measure.; UK operations and FCA status were out of scope.).

Read the [full reliability assessment](https://spot.insure/insurance-providers/simply-business/reliability).

## Pie Insurance Reviews

Review Score: 1.7 / 10 from 2 rated sources, equally weighted.

Pie’s service record raises clear concerns: elevated regulator complaints reported by NerdWallet, 1.7/5 on Trustpilot and an F from BBB. Investigate billing, cancellation and complaint handling before buying.

- Trustpilot: TrustScore 1.7 (5 stars); 666 reviews. Brand-level Trustpilot consumer reviews; policy product is generally identified as workers’ compensation, but reviewer policy/entity scope varies. Checked 2026-09-25. [Pie Insurance Reviews - Trustpilot](https://www.trustpilot.com/review/www.pieinsurance.com)
- BBB: BBB Rating F (BBB letter grade). BBB profile for commercial insurance services; BBB grade and complaint-response record, not policy performance measure. Period: BBB profile reports 15 complaints filed, 13 unanswered; complaint data, not reviews. Checked 2026-09-25. [Pie Insurance Services | BBB Business Profile](https://www.bbb.org/us/dc/washington/profile/commercial-insurance-services/pie-insurance-services-0241-236060990)

Reviewed 2026-09-25. [Read the sourced review](https://spot.insure/insurance-providers/pie-insurance/reviews).

## Simply Business Reviews

Review Score: 5.7 / 10 from 4 rated sources, equally weighted.

Customers disagree about Simply Business. Trustpilot shows 4.3 out of 5 from 1,901 reviews, but BBB customers give it 1.95 from 20 reviews and ConsumerAffairs shows 1.0.

- Trustpilot: TrustScore 4.3 (out of 5); 1901 reviews. Simply Business US Trustpilot profile. Reviews are not tied to a specific insurance line or insurer. Period: profile accessed 2026-09-29; 419 in last 12 months. Checked 2026-09-29. [Simply Business US Reviews](https://www.trustpilot.com/review/simplybusiness.com)
- ConsumerAffairs: ConsumerAffairs header rating 1.0 (out of 5 (breakdown conflicts with review filters)); 148 reviews. ConsumerAffairs Simply Business page, broad business-insurance context; not line-specific. Period: page updated 2026-09-17; denominator unresolved. Checked 2026-09-29. [Simply Business Reviews](https://www.consumeraffairs.com/insurance/simply-business.html)
- BBB: BBB business grade B+ (BBB letter grade). BBB profile classifies Simply Business as an insurance agency; business grade, consumer-review average and complaint ledger are separate measures, none is line-specific. Period: profile accessed 2026-09-29. Checked 2026-09-29. [Simply Business BBB Business Profile](https://www.bbb.org/us/ma/boston/profile/insurance-agency/simply-business-0021-539591); [Simply Business BBB Complaints](https://www.bbb.org/us/ma/boston/profile/insurance-agency/simply-business-0021-539591/complaints); [Simply Business BBB Customer Reviews](https://www.bbb.org/us/ma/boston/profile/insurance-agency/simply-business-0021-539591/customer-reviews)
- BBB: BBB customer review average 1.95 (out of 5); 20 reviews. BBB customer-review average for the Simply Business profile (Boston, MA). Separate from the business grade. Period: BBB review page checked 2026-09-29. Checked 2026-09-29. [Simply Business BBB Customer Reviews](https://www.bbb.org/us/ma/boston/profile/insurance-agency/simply-business-0021-539591/customer-reviews)

Reviewed 2026-09-29. [Read the sourced review](https://spot.insure/insurance-providers/simply-business/reviews).

## Introduction

This comparison pairs small businesses through Pie Insurance with small businesses through Simply Business. Their coverage catalogues share business owners’ policy, cyber, general liability. If one of those lines fits your business, compare the proposed forms and quote routes side by side; listed lines do not establish equal policy terms or eligibility. [3](https://www.pieinsurance.com/workers-comp "Workers’ Comp Insurance For Small Businesses") [26](https://www.simplybusiness.com/about-us/ "Our Small Business Insurance Story")



## Coverage Comparison

| Coverage Type | Pie Insurance | Simply Business |
| --- | --- | --- |
| [Business owner’s policy](https://spot.insure/coverage/business-owners-policy) | Listed: Pie accepts business owner’s policy quote requests. [7](https://www.pieinsurance.com/small-business-insurance/business-owners-policy "Business Owner’s Policy") | Listed [35](https://www.simplybusiness.com/business-insurance/business-owners-policy-insurance/ "Business Owner’s Policy Insurance") |
| [Commercial property](https://spot.insure/coverage/commercial-property) | Not listed | Listed: Offered as part of a BOP, rather than as a standalone policy. [36](https://www.simplybusiness.com/business-insurance/business-owners-policy-insurance/commercial-property-insurance/ "Commercial Property Insurance") [35](https://www.simplybusiness.com/business-insurance/business-owners-policy-insurance/ "Business Owner’s Policy Insurance") |
| [Cyber liability](https://spot.insure/coverage/cyber) | Listed: Pie provides access to cyber insurance quotes from carrier partners. [8](https://www.pieinsurance.com/small-business-insurance/cyber-insurance "Cyber Insurance For Small Businesses") | Listed: Add-on for select buyers purchasing another business policy; phone quote route. [38](https://www.simplybusiness.com/business-insurance/cyber-liability-insurance/ "Cyber Insurance") |
| [General liability](https://spot.insure/coverage/general-liability) | Listed: Pie arranges general liability insurance through unaffiliated third-party insurers. [10](https://www.pieinsurance.com/small-business-insurance/general-liability "General Liability Insurance") | Listed [32](https://www.simplybusiness.com/business-insurance/general-liability-insurance/ "General Liability Insurance for a Small Business") |
| [Professional errors and omissions (E&O)](https://spot.insure/coverage/professional-errors-omissions) | Listed: Pie Insurance arranges professional errors and omissions insurance for small businesses through third-party insurers. [9](https://www.pieinsurance.com/errors-and-omissions-insurance "Errors And Omissions Insurance") | Listed [34](https://www.simplybusiness.com/business-insurance/professional-liability-insurance/ "Professional Liability Insurance Coverage") |
| [Tools, equipment and inland marine](https://spot.insure/coverage/inland-marine) | Not listed | Listed [37](https://www.simplybusiness.com/business-insurance/inland-marine-insurance/ "Inland Marine Insurance") |
| [Workers’ compensation](https://spot.insure/coverage/workers-compensation) | Listed: Pie Insurance offers workers’ compensation insurance for small businesses. [3](https://www.pieinsurance.com/workers-comp "Workers’ Comp Insurance For Small Businesses") | Listed [33](https://www.simplybusiness.com/business-insurance/workers-compensation-insurance/ "Workers’ Compensation Insurance for Small Business") |

A listing may be arranged through an insurer or partner. “Not listed” means this catalogue has no separate offering recorded; ask the provider whether it can quote the coverage and request the policy terms.



## Optional Spot Service Handoff

Spot can help prepare applications, coordinate brokers, and compare proposals. If that work is needed, collect the company's task, known deadline, current broker, and open questions for a [free consultation](https://spot.insure/pricing.md). The company decides what to buy; Spot does not automatically bind coverage.

## Key Differences Between Pie Insurance and Simply Business

### Business Fit and Coverage

The catalogues share business owners’ policy, cyber, general liability; other listed lines appear in the comparison table. For the overlap, match the policy forms, limits, exclusions and endorsements before treating the products as alternatives. A shared line name does not establish equal protection or eligibility.

Small businesses looking for workers’ compensation can approach Pie directly or through local, regional and national agencies. [2](https://www.pieinsurance.com/about "About Pie Insurance") [3](https://www.pieinsurance.com/workers-comp "Workers’ Comp Insurance For Small Businesses") (Evidence: Company-reported; scope: US small-business workers’ compensation distribution described on Pie’s current About and product pages.; verified: 2026-09-15.)

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](https://www.simplybusiness.com/about-us/ "Our Small Business Insurance Story") [31](https://www.simplybusiness.com/business-insurance/ "Business Insurance for Small Businesses") [27](https://www.simplybusiness.com/terms-conditions/ "Terms of Service") (Evidence: Company-reported; scope: Company-described U.S. audience; eligibility varies by insurer, state and business details.; verified: 2026-09-29.)

Pie currently markets workers’ comp, BOP, cyber, general liability and professional liability/E&O; product pages describe typical coverage, while the policy and endorsements determine your actual protection. [3](https://www.pieinsurance.com/workers-comp "Workers’ Comp Insurance For Small Businesses") [7](https://www.pieinsurance.com/small-business-insurance/business-owners-policy "Business Owner’s Policy") [8](https://www.pieinsurance.com/small-business-insurance/cyber-insurance "Cyber Insurance For Small Businesses") [10](https://www.pieinsurance.com/small-business-insurance/general-liability "General Liability Insurance") [9](https://www.pieinsurance.com/errors-and-omissions-insurance "Errors And Omissions Insurance") [4](https://www.pieinsurance.com/legal/terms-of-use "Terms Of Use") (Evidence: Company-reported; scope: Public US Pie pages with an explicit quote or contact invitation; educational-only topics and components of a BOP were not counted as standalone offerings.; verified: 2026-09-15.)

### Roles and Quote Access

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](https://www.pieinsurance.com/about "About Pie Insurance") [5](https://www.pieinsurance.com/legal "Legal") [3](https://www.pieinsurance.com/workers-comp "Workers’ Comp Insurance For Small Businesses") [7](https://www.pieinsurance.com/small-business-insurance/business-owners-policy "Business Owner’s Policy") [8](https://www.pieinsurance.com/small-business-insurance/cyber-insurance "Cyber Insurance For Small Businesses") [9](https://www.pieinsurance.com/errors-and-omissions-insurance "Errors And Omissions Insurance") [10](https://www.pieinsurance.com/small-business-insurance/general-liability "General Liability Insurance") (Evidence: Company-reported; scope: 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.; verified: 2026-09-15.)

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](https://www.simplybusiness.com/about-us/ "Our Small Business Insurance Story") [27](https://www.simplybusiness.com/terms-conditions/ "Terms of Service") [39](https://www.travelers.com/about-travelers/producer-compensation-disclosure "Producer Compensation Disclosure (United States)") [28](https://www.simplybusiness.com/contact-us/ "Contact Us") (Evidence: Company-reported; scope: 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.; verified: 2026-09-29.)

Have your ZIP, payroll and class-code details ready for a Pie workers’ compensation quote; its online intake begins with ZIP code. [6](https://quote.pieinsurance.com/ "Pie Insurance — Quote") [3](https://www.pieinsurance.com/workers-comp "Workers’ Comp Insurance For Small Businesses") (Evidence: Company-reported; scope: Unauthenticated first step and Pie’s description of workers’ compensation quote inputs; no data was entered and the flow was not advanced.; verified: 2026-09-15.)

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](https://www.simplybusiness.com/contact-us/ "Contact Us") [27](https://www.simplybusiness.com/terms-conditions/ "Terms of Service") (Evidence: Company-reported; scope: Published U.S. quote and service channels. Binding depends on panel-member approval and the individual offer.; verified: 2026-09-29.)

Use these routes to plan who will assemble the submission and whether you can complete the purchase online or need an agent or broker. Ask Pie Insurance and Simply Business to confirm the route for your state, coverage and business details; an online quote path alone does not show that a risk can be bound. [6](https://quote.pieinsurance.com/ "Pie Insurance — Quote") [28](https://www.simplybusiness.com/contact-us/ "Contact Us")

### Policy Service and Claims

Pie policyholders can manage payments, download documents and request workers’ comp certificates online; custom certificates may require your agent. [15](https://www.pieinsurance.com/resource-center/online-account-tutorial "Online Account Tutorial") [16](https://www.pieinsurance.com/workers-comp/resources/frequently-asked-questions "Workers’ Comp FAQs") (Evidence: Company-reported; scope: Published workers’ compensation account tutorial; authenticated features were not accessed or independently tested.; verified: 2026-09-15.)

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](https://www.simplybusiness.com/contact-us/ "Contact Us") [29](https://www.simplybusiness.com/help-center/ "Help Center") [27](https://www.simplybusiness.com/terms-conditions/ "Terms of Service") (Evidence: Company-reported; scope: Company-described post-purchase service paths; available tasks may depend on policy and insurer.; verified: 2026-09-29.)

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. [20](https://www.pieinsurance.com/claims "File Your Claim Within 24 Hours") (Evidence: Company-reported; scope: Published first-report process for Pie-serviced workers’ compensation claims; state notice rules and the issuing carrier’s policy still apply.; verified: 2026-09-15.)

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](https://www.simplybusiness.com/terms-conditions/ "Terms of Service") [29](https://www.simplybusiness.com/help-center/ "Help Center") (Evidence: Company-reported; scope: General site-policy claim responsibility. Harborway/Spinnaker applies only to the named Harborway placement relationship.; verified: 2026-09-29.)

Compare the practical handoffs for documents, policy changes, renewal questions and claim notices. A listed support route describes access to help, not a claim outcome or a guarantee of service speed.

## What to Confirm in Quotes

Request quotes for the same business details, coverage lines, limits, deductibles or retentions and policy period. Ask Pie Insurance and Simply Business to name the producer and issuing insurer for each proposed policy, confirm who can bind it, and itemize any customer fees or intermediary compensation. For the overlapping business owners’ policy, cyber, general liability, compare the actual insuring agreement, exclusions, sublimits and endorsements. Also confirm who handles account changes and receives claim notices. [5](https://www.pieinsurance.com/legal "Legal") [26](https://www.simplybusiness.com/about-us/ "Our Small Business Insurance Story") [17](https://www.pieinsurance.com/payment-options "Payment Options") [27](https://www.simplybusiness.com/terms-conditions/ "Terms of Service")

## Compare Services

What each provider documents about the services you may need.

| Criteria | Pie Insurance | Simply Business |
| --- | --- | --- |
| Business role | 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](https://www.pieinsurance.com/about "About Pie Insurance") [5](https://www.pieinsurance.com/legal "Legal") [3](https://www.pieinsurance.com/workers-comp "Workers’ Comp Insurance For Small Businesses") [7](https://www.pieinsurance.com/small-business-insurance/business-owners-policy "Business Owner’s Policy") [8](https://www.pieinsurance.com/small-business-insurance/cyber-insurance "Cyber Insurance For Small Businesses") [9](https://www.pieinsurance.com/errors-and-omissions-insurance "Errors And Omissions Insurance") [10](https://www.pieinsurance.com/small-business-insurance/general-liability "General Liability Insurance") (Evidence: Company-reported; scope: 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.; verified: 2026-09-15.)<br><br>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](https://www.pieinsurance.com/legal/terms-of-use "Terms Of Use") [24](https://insurance.illinois.gov/applications/RegEntPortal/ViewEntityDetails.aspx?en=982281&s=Active&t=INS "Pie Casualty Insurance Company — Entity Details") [22](https://ratings.ambest.com/DisclosurePDF.aspx?AMBNum=12272&PCA=0 "AM Best Rating Disclosure Report — Pie Casualty Insurance Company") (Evidence: Verified; scope: Website ownership and the parent shown for Pie Casualty Insurance Company; no claim about voting control or every intermediate subsidiary.; verified: 2026-09-15.)<br><br>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](https://www.pieinsurance.com/legal "Legal") [25](https://oci.wi.gov/Pages/PressReleases/AdminActions202401.aspx "Administrative Actions — January 2024") (Evidence: Company-reported; scope: Producer identity and Pie-published US license list; Wisconsin’s regulator separately identifies this entity in a 2024 administrative action.; verified: 2026-09-15.) | 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](https://www.simplybusiness.com/about-us/ "Our Small Business Insurance Story") [27](https://www.simplybusiness.com/terms-conditions/ "Terms of Service") [39](https://www.travelers.com/about-travelers/producer-compensation-disclosure "Producer Compensation Disclosure (United States)") [28](https://www.simplybusiness.com/contact-us/ "Contact Us") (Evidence: Company-reported; scope: 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.; verified: 2026-09-29.) |
| Application process | Small businesses can start a workers’ compensation quote online or through an insurance agent; agencies use a separate partner portal. [2](https://www.pieinsurance.com/about "About Pie Insurance") [1](https://www.pieinsurance.com/ "Pie Insurance") [3](https://www.pieinsurance.com/workers-comp "Workers’ Comp Insurance For Small Businesses") (Evidence: Company-reported; scope: 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.; verified: 2026-09-15.)<br><br>Have your ZIP, payroll and class-code details ready for a Pie workers’ compensation quote; its online intake begins with ZIP code. [6](https://quote.pieinsurance.com/ "Pie Insurance — Quote") [3](https://www.pieinsurance.com/workers-comp "Workers’ Comp Insurance For Small Businesses") (Evidence: Company-reported; scope: Unauthenticated first step and Pie’s description of workers’ compensation quote inputs; no data was entered and the flow was not advanced.; verified: 2026-09-15.)<br><br>Pie advertises a workers’ compensation quote in about three minutes, but this company estimate does not predict underwriting or binding time. [3](https://www.pieinsurance.com/workers-comp "Workers’ Comp Insurance For Small Businesses") [1](https://www.pieinsurance.com/ "Pie Insurance") (Evidence: Company-reported; scope: Workers’ compensation quote marketing; no timed independent quote test was performed.; verified: 2026-09-15.) | 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](https://www.simplybusiness.com/contact-us/ "Contact Us") [27](https://www.simplybusiness.com/terms-conditions/ "Terms of Service") (Evidence: Company-reported; scope: Published U.S. quote and service channels. Binding depends on panel-member approval and the individual offer.; verified: 2026-09-29.) |
| Servicing and renewals | Pie policyholders can manage payments, download documents and request workers’ comp certificates online; custom certificates may require your agent. [15](https://www.pieinsurance.com/resource-center/online-account-tutorial "Online Account Tutorial") [16](https://www.pieinsurance.com/workers-comp/resources/frequently-asked-questions "Workers’ Comp FAQs") (Evidence: Company-reported; scope: Published workers’ compensation account tutorial; authenticated features were not accessed or independently tested.; verified: 2026-09-15.)<br><br>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. [19](https://www.pieinsurance.com/workers-comp/premium-audit "Your Workers’ Comp Premium Audit") (Evidence: Company-reported; scope: Pie workers’ compensation premium audit process; the page does not quantify any resulting additional charge or refund.; verified: 2026-09-15.)<br><br>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](https://www.pieinsurance.com/workers-comp/resources/frequently-asked-questions "Workers’ Comp FAQs") [21](https://www.pieinsurance.com/agency/faq "Partner FAQ") (Evidence: Company-reported; scope: Different company-published consumer and agency descriptions of workers’ compensation renewal. Neither guarantees renewal or unchanged terms; the account notice determines the applicable process.; verified: 2026-09-29.) | 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. [28](https://www.simplybusiness.com/contact-us/ "Contact Us") (Evidence: Company-reported; scope: Hours displayed on the current U.S. contact page; no actual wait-time observation is implied.; verified: 2026-09-29.)<br><br>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](https://www.simplybusiness.com/contact-us/ "Contact Us") [29](https://www.simplybusiness.com/help-center/ "Help Center") [27](https://www.simplybusiness.com/terms-conditions/ "Terms of Service") (Evidence: Company-reported; scope: Company-described post-purchase service paths; available tasks may depend on policy and insurer.; verified: 2026-09-29.)<br><br>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](https://www.simplybusiness.com/help-center/ "Help Center") [27](https://www.simplybusiness.com/terms-conditions/ "Terms of Service") (Evidence: Conflicting sources; scope: Company-published descriptions reviewed 2026-09-29. FAQ detail, Help Center summary and Terms are inconsistent; no buyer-specific policy notice was reviewed.; verified: 2026-09-29.) |
| Claims assistance | 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. [20](https://www.pieinsurance.com/claims "File Your Claim Within 24 Hours") (Evidence: Company-reported; scope: Published first-report process for Pie-serviced workers’ compensation claims; state notice rules and the issuing carrier’s policy still apply.; verified: 2026-09-15.)<br><br>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](https://www.pieinsurance.com/agency/faq "Partner FAQ") [11](https://www.pieinsurance.com/agency/states-we-serve "Workers’ Comp Coverage By State") [22](https://ratings.ambest.com/DisclosurePDF.aspx?AMBNum=12272&PCA=0 "AM Best Rating Disclosure Report — Pie Casualty Insurance Company") (Evidence: Conflicting sources; scope: Public allocation of workers’ compensation claim handling; the current handler for an individual policy should be taken from its state kit and claim instructions.; verified: 2026-09-15.) | 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](https://www.simplybusiness.com/terms-conditions/ "Terms of Service") [29](https://www.simplybusiness.com/help-center/ "Help Center") (Evidence: Company-reported; scope: General site-policy claim responsibility. Harborway/Spinnaker applies only to the named Harborway placement relationship.; verified: 2026-09-29.) |
| Customer focus | Small businesses looking for workers’ compensation can approach Pie directly or through local, regional and national agencies. [2](https://www.pieinsurance.com/about "About Pie Insurance") [3](https://www.pieinsurance.com/workers-comp "Workers’ Comp Insurance For Small Businesses") (Evidence: Company-reported; scope: US small-business workers’ compensation distribution described on Pie’s current About and product pages.; verified: 2026-09-15.) | 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](https://www.simplybusiness.com/about-us/ "Our Small Business Insurance Story") [31](https://www.simplybusiness.com/business-insurance/ "Business Insurance for Small Businesses") [27](https://www.simplybusiness.com/terms-conditions/ "Terms of Service") (Evidence: Company-reported; scope: Company-described U.S. audience; eligibility varies by insurer, state and business details.; verified: 2026-09-29.) |
| Fees and compensation | 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](https://www.pieinsurance.com/payment-options "Payment Options") [18](https://www.pieinsurance.com/pay-as-you-go "Pay-As-You-Go With Pie Insurance") (Evidence: Company-reported; scope: Pie’s current workers’ compensation payment pages; actual availability and policy-specific charges need confirmation in the quote.; verified: 2026-09-15.)<br><br>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. [17](https://www.pieinsurance.com/payment-options "Payment Options") (Evidence: Company-reported; scope: Credit-card payments for new single-state workers’ compensation policies under the current payment-options page.; verified: 2026-09-15.)<br><br>Ask the state-specific price before requesting a waiver of subrogation because Pie charges for each specific or blanket waiver but publishes no amount. [16](https://www.pieinsurance.com/workers-comp/resources/frequently-asked-questions "Workers’ Comp FAQs") (Evidence: Not publicly disclosed; scope: Workers’ compensation waiver requests through Pie’s published service process.; verified: 2026-09-15.)<br><br>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](https://www.pieinsurance.com/agency/faq "Partner FAQ") [5](https://www.pieinsurance.com/legal "Legal") (Evidence: Not publicly disclosed; scope: Agency-distributed workers’ compensation and other third-party placements; expired promotional incentives were not treated as current standard compensation.; verified: 2026-09-15.) | 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. [27](https://www.simplybusiness.com/terms-conditions/ "Terms of Service") (Evidence: Company-reported; scope: General disclosure dated 2026-06-30; no specific commission, fee schedule, premium or customer charge was reviewed.; verified: 2026-09-29.) |

## Related Reading

- [What Is Pie Insurance?](https://spot.insure/insurance-providers/pie-insurance)
- [Simply Business: Online Small-Business Insurance Marketplace](https://spot.insure/insurance-providers/simply-business)

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## Sources

### [Pie Insurance Official Website](https://www.pieinsurance.com/)

1. [Pie Insurance](https://www.pieinsurance.com/). Pie Insurance; Homepage: small-business audience; direct workers’ compensation quote; online account; footer entity, insurer and availability qualifications. Accessed 2026-09-15.
2. [About Pie Insurance](https://www.pieinsurance.com/about). Pie Insurance; About Pie; direct and agency distribution; footer legal disclosure. Accessed 2026-09-15.
3. [Workers’ Comp Insurance For Small Businesses](https://www.pieinsurance.com/workers-comp). Pie Insurance; Get a workers’ compensation quote online; insurance made for your small business; quote inputs; coverage description; quote-time and savings qualifications; AM Best link. Accessed 2026-09-16.
4. [Terms Of Use](https://www.pieinsurance.com/legal/terms-of-use). Pie Insurance; Updated 26 April 2022; Ownership and Agreement to Terms; geographic and product eligibility; policy controls coverage. Accessed 2026-09-15.
5. [Legal](https://www.pieinsurance.com/legal). Pie Insurance; State Licenses; footer disclosure naming producer and workers’ compensation versus third-party underwriting roles. Accessed 2026-09-15.
6. [Pie Insurance — Quote](https://quote.pieinsurance.com/). Pie Insurance; First step: Business ZIP Code. Accessed 2026-09-15.
7. [Business Owner’s Policy](https://www.pieinsurance.com/small-business-insurance/business-owners-policy). Pie Insurance; BOP definition; typical components; Make sure you’re covered: Start your BOP quote; footer third-party insurer qualification. Accessed 2026-09-16.
8. [Cyber Insurance For Small Businesses](https://www.pieinsurance.com/small-business-insurance/cyber-insurance). Pie Insurance; First- and third-party descriptions; carrier-partner quote invitation; policy-variation qualification. Accessed 2026-09-16.
9. [Errors And Omissions Insurance](https://www.pieinsurance.com/errors-and-omissions-insurance). Pie Insurance; Errors and Omissions Insurance hero (E&O and professional liability equivalence); typical claims; Make sure you’re covered: insurance carrier partners, Start now; footer third-party professional liability insurers. Accessed 2026-09-16.
10. [General Liability Insurance](https://www.pieinsurance.com/small-business-insurance/general-liability). Pie Insurance; Typical covered categories; Make sure you are covered: carrier-partner quote invitation; legal footer: third-party insurers not affiliated with Pie. Accessed 2026-09-16.
11. [Workers’ Comp Coverage By State](https://www.pieinsurance.com/agency/states-we-serve). Pie Insurance; Headline says 40 states and the District of Columbia; rendered state selector listed 39 state names and omitted New York and D.C. Accessed 2026-09-15.
12. [Agency Document Library](https://www.pieinsurance.com/agency/document-library). Pie Insurance; Workers’ Comp State Documents: 40 named states plus Washington, D.C. Accessed 2026-09-15.
13. [Pie Insurance Reports Strong 2025](https://www.pieinsurance.com/resource-center/press/2025-year-in-review). Pie Insurance; 13 January 2026 release; Key 2025 Milestones says 39 states plus Washington, D.C.; company and distribution description. Accessed 2026-09-15.
14. [Commercial Auto Claim FAQs](https://www.pieinsurance.com/claims/comm-auto-faq). Pie Insurance; Does Pie offer commercial auto insurance?; submission cutoff 1 December 2025; no new or renewal policies on or after 1 January 2026; legacy claim guidance. Accessed 2026-09-15.
15. [Online Account Tutorial](https://www.pieinsurance.com/resource-center/online-account-tutorial). Pie Insurance; Payment-method updates; instant and custom certificates; policy information; document access; agent-handled custom certificate qualification. Accessed 2026-09-15.
16. [Workers’ Comp FAQs](https://www.pieinsurance.com/workers-comp/resources/frequently-asked-questions). Pie Insurance; Certificates; specific and blanket waiver requests, two-business-day response and state-dependent charge; Billing & Payments; Policy Renewal / When will I know it’s time to renew my policy? (approximately 30 days before expiry, quote for review and acceptance); Annual Audit; Claims. Accessed 2026-09-29.
17. [Payment Options](https://www.pieinsurance.com/payment-options). Pie Insurance; Annual, semi-annual, quarterly, monthly and pay-as-you-go schedules; payment methods; 3% card fee and state exceptions. Accessed 2026-09-15.
18. [Pay-As-You-Go With Pie Insurance](https://www.pieinsurance.com/pay-as-you-go). Pie Insurance; No initial deposit; actual-payroll monthly premium; automatic deductions; payroll-provider coordination. Accessed 2026-09-15.
19. [Your Workers’ Comp Premium Audit](https://www.pieinsurance.com/workers-comp/premium-audit). Pie Insurance; Required annual audit; estimated versus actual payroll; audit partner; requested payroll, employee, cash-expense and subcontractor certificate records. Accessed 2026-09-15.
20. [File Your Claim Within 24 Hours](https://www.pieinsurance.com/claims). Pie Insurance; Workers’ compensation reporting by online form, 24/7 phone or email; information requested; post-report coverage determination. Accessed 2026-09-15.
21. [Partner FAQ](https://www.pieinsurance.com/agency/faq). Pie Insurance; How does Pie handle claims? (workers’ compensation in 34 states; CorVel in Alaska, Mississippi, Nevada, New Mexico and Oregon); How does Pie pay commissions? (new and renewing policies, earned premium); How does Pie handle renewals? (30-day preview: under $20,000 to insured with agency copied, over $20,000 to producer; unless otherwise notified, deposit draft and renewal issuance five days before effective date; exact $20,000 case unstated); Renewal Billing. Accessed 2026-09-29.
22. [AM Best Rating Disclosure Report — Pie Casualty Insurance Company](https://ratings.ambest.com/DisclosurePDF.aspx?AMBNum=12272&PCA=0). AM Best Rating Services, Inc.; Page 1: A- (Excellent), Stable, affirmed 24 April 2026; page 14: rating unit, group insurer acquisitions, 100% workers’ compensation writing through PCIC and TPIC from 1 January 2024, 40 states and D.C. Accessed 2026-09-15.
23. [The Pie Insurance Company — Company Details](https://insurance.mo.gov/find-insurance-company/company-details?id=104347111). Missouri Department of Commerce and Insurance; Company name; active license status; NAIC 21857; property-and-casualty authority; 2025 workers’ compensation market data. Accessed 2026-09-15.
24. [Pie Casualty Insurance Company — Entity Details](https://insurance.illinois.gov/applications/RegEntPortal/ViewEntityDetails.aspx?en=982281&s=Active&t=INS). Illinois Department of Insurance; Legal name; P&C Domestic Stock; active status; NAIC 10997; Pie Group Holdings, Inc. parent. Accessed 2026-09-15.
25. [Administrative Actions — January 2024](https://oci.wi.gov/Pages/PressReleases/AdminActions202401.aspx). Wisconsin Office of the Commissioner of Insurance; Allegations and Actions Against Companies: Pie Insurance Services, Inc. agreed to add a disclaimer to its “save up to 30%” advertising claim after misleading-advertising allegations. Accessed 2026-09-15.

### [Simply Business Official Website](https://www.simplybusiness.com/)

26. [Our Small Business Insurance Story](https://www.simplybusiness.com/about-us/). Simply Business; Opening description and audience; digital marketplace, business types and U.S. service. Accessed 2026-09-29.
27. [Terms of Service](https://www.simplybusiness.com/terms-conditions/). Simply Business; Dated June 30, 2026; §1 lines 22–28; §8 lines 87–113; §10 lines 143–149; §19 line 211. Accessed 2026-09-29.
28. [Contact Us](https://www.simplybusiness.com/contact-us/). Simply Business; Opening contact details lines 20–31; licensed-agent phone hours lines 46–59; U.S. licensing and state-specific name disclosures in footer lines 108–111, including California License #0M20593. Accessed 2026-09-29.
29. [Help Center](https://www.simplybusiness.com/help-center/). Simply Business; Claims, account servicing, agent-routed changes, renewal FAQ and Common Topics. Accessed 2026-09-29.
30. [How Simply Business Works](https://www.simplybusiness.com/about-us/how-simply-business-works/). Simply Business; Common types lines 92–160; quote/purchase flow; estimate-method footnotes lines 198–200. Accessed 2026-09-29.
31. [Business Insurance for Small Businesses](https://www.simplybusiness.com/business-insurance/). Simply Business; Small Business Insurance Coverage Options and policy links. Accessed 2026-09-29.
32. [General Liability Insurance for a Small Business](https://www.simplybusiness.com/business-insurance/general-liability-insurance/). Simply Business; Coverage lines 51–75; audience lines 61–65, 153–155; application and examples elsewhere on page. Accessed 2026-09-29.
33. [Workers’ Compensation Insurance for Small Business](https://www.simplybusiness.com/business-insurance/workers-compensation-insurance/). Simply Business; Coverage and benefits lines 45–69; state/buyer qualifications lines 178–189. Accessed 2026-09-29.
34. [Professional Liability Insurance Coverage](https://www.simplybusiness.com/business-insurance/professional-liability-insurance/). Simply Business; Coverage lines 45–100; buyer examples lines 101–158; online quote steps lines 237–260. Accessed 2026-09-29.
35. [Business Owner’s Policy Insurance](https://www.simplybusiness.com/business-insurance/business-owners-policy-insurance/). Simply Business; Bundle lines 34–38, 218–243; add-on/exclusion discussion lines 226–243; buyer and quote sections. Accessed 2026-09-29.
36. [Commercial Property Insurance](https://www.simplybusiness.com/business-insurance/business-owners-policy-insurance/commercial-property-insurance/). Simply Business; Lines 15–18 present physical-location cover as part of a BOP; lines 34–49 describe the package; lines 59–63 say it is offered as part of the BOP rather than as a standalone policy and link to a BOP quote. Accessed 2026-09-29.
37. [Inland Marine Insurance](https://www.simplybusiness.com/business-insurance/inland-marine-insurance/). Simply Business; Equipment/inventory lines 15–18, 59–63; examples and quote workflow lines 97–140, 168–191. Accessed 2026-09-29.
38. [Cyber Insurance](https://www.simplybusiness.com/business-insurance/cyber-liability-insurance/). Simply Business; Claim types lines 88–105; select-buyer add-on/phone quote lines 171–175; route and last-updated lines 389–395. Accessed 2026-09-29.
39. [Producer Compensation Disclosure (United States)](https://www.travelers.com/about-travelers/producer-compensation-disclosure). Travelers; Ownership interest in a producer, lines 57–60: Travelers says it owns Simply Business, Inc.; relation to Simply Business, LLC not stated. Accessed 2026-09-29.

Updated 2026-09-30. Spot, a product of Tools for Enlightenment, publishes this research and works in the commercial insurance market. [Editorial policy](https://spot.insure/editorial-policy). To suggest a correction, [contact Spot](https://spot.insure/contact) with the page URL and supporting source.

## Agent and Developer Resources

- [Markdown page](https://spot.insure/compare/pie-insurance-vs-simply-business.md)
- [Developer resources](https://spot.insure/developers)
- [Public MCP server](https://spot.insure/mcp)
- [MCP server manifest](https://spot.insure/server.json)
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- [Public page index](https://spot.insure/llms.txt)