Pie Insurance vs Resilience

Separate Pie’s payroll-based workers’ compensation program and partner cyber route from Resilience’s specialist cyber offering.

Introduction

Hiring employees and signing a customer cyber clause can send a founder shopping for two policies at once. Pie's main workers' compensation program and its partner cyber offering use different underwriting routes. Resilience supplies a specialist cyber and technology E&O comparison, not a substitute for the payroll-related insurance purchase. 5 3 8 26

Where Each Provider Shines

Where Pie Insurance Shines

  • Small businesses can start a workers’ compensation quote directly online or through an insurance agent. 2,1,3
  • Workers’ compensation payment options include pay-as-you-go using reported payroll, with no initial deposit. 17,18

Where Resilience Shines

  • Technology E&O for software, hardware and technology services 29
  • Financial risk prioritization and multi-entity cyber visibility 33,34

Coverage Comparison

Coverage TypePie InsuranceResilience
Business owner’s policyListed 7Not listed
Cyber liabilityListed 8Listed 28
General liabilityListed 10Not listed
Professional liability / E&OListed 9Not listed
Technology errors and omissionsNot listedListed 29
Workers’ compensationListed 3Not listed

Listed products and programs, including policies arranged through insurers or partners. Optional endorsements are discussed in the analysis below. “Not listed” means no separate offering appears in the reviewed catalogue; confirm availability and policy terms with the provider.

Key Differences Between Pie Insurance and Resilience

Do Not Carry the Workers’ Compensation Insurer Into Cyber

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. 5,7,8,9,10

Pie identifies affiliated insurers for workers' compensation, but that does not identify the company on a cyber proposal or transfer their rating to an unnamed partner. Resilience names Homeland alternatives in its US disclosure. Ask for each cyber quote's legal insurer before comparing financial-strength requirements or policy terms. 5 22 27

Payroll Administration Does Not Describe a Cyber Renewal

Pie's pay-as-you-go option uses reported payroll, and its workers' compensation program requires an annual audit. Those are specific to that program; the reviewed public documentation does not establish them as a way to pay for or renew Pie partner cyber insurance. Resilience's reviewed sources leave standard renewal requirements unspecified. Build separate information checklists for payroll and cyber underwriting. 18 19 30

If the startup also needs technology liability, Pie's generic professional-liability offer is not proof of identical scope to Resilience's technology E&O. Resilience's stated technology revenue appetite can itself be a constraint for an early-stage company. Request activity-specific eligibility rather than assuming the presence of E&O in a catalogue resolves it. 9 29

Keep Workplace Injury and Cyber Reporting Separate

Pie publishes workers' compensation reporting and state-dependent claims-handling arrangements. Resilience describes a cyber claims manager and external response specialists. Do not use Pie's workplace-injury instructions as the presumed cyber notice route; obtain the partner policy's instructions. The public sources do not establish a quality ranking between those unrelated claims functions. 20 21 31

What to Confirm in Quotes

Ask Pie to identify its proposed cyber insurer, complete form and service contacts independently of the workers' compensation account. Ask Resilience whether the startup qualifies for cyber, technology E&O or both and how California placement would work. Budget payroll adjustments and cyber retentions separately; combining the shopping exercise does not merge the contracts. 8 4 29 27

Service Comparison

Pie Insurance vs Resilience: documented services and availability

CriteriaPie InsuranceResilience
Business role

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. 2,5,3,7,8,9,10

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. 4,24,22

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. 5,25

Resilience combines cyber insurance and technology errors and omissions insurance with cybersecurity risk-management services. 26,28,29

Resilience identifies Ocrea Risk Services, LLC, doing business as Resilience Cyber Insurance Solutions, as its US insurance distributor and lists NPN 19169260. This company disclosure is not independent verification of a California license. 27

Access to insurers

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. 5,22,23,24

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. 22

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. 5,7,8,9,10

Resilience’s US disclosure names Homeland Insurance Company of New York or Homeland Insurance Company of Delaware as underwriting insurers. It does not specify which would issue a particular California quote. 27

Application process

A small business can start a workers’ compensation quote on Pie’s website or work through an insurance agent; appointed agencies use a separate partner portal. 2,1,3

The live direct quote starts with the business ZIP code. Pie’s workers’ compensation page says applicants also need their name, business name, annual payroll and class-code information. 6,3

Pie advertises an online workers’ compensation quote in about three minutes, while expressly stating that individual quote times vary. This is a company claim and does not establish how long underwriting or binding will take for a particular risk. 3,1

Resilience presents insurance to brokers through a dedicated broker page and offers a public contact route for product inquiries. The reviewed pages do not document an end-to-end self-service purchase or a guaranteed quote or binding time. 30,32

Servicing and renewals

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. 15,16

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. 19

Pie says it sends a workers’ compensation renewal quote about 30 days before the current term ends for the policyholder’s review and acceptance. 16

Resilience markets Edge for prioritizing security spending by estimated financial impact, and Arc for viewing cyber risk across multiple entities. These are risk-management services, not additional insurance coverage lines. 33,34

Resilience states that buying insurance is not tied to buying security services. Confirm which services are included in the proposed package and which require a separate agreement. 27

The current broker and product pages reviewed do not specify renewal documentation, a renewal price commitment or a standard servicing turnaround. 30,28,29

Claims assistance

Pie asks policyholders to report a workplace injury within 24 hours through its online form, 24/7 phone line or email. After intake, it says a claims professional follows up, determines whether the policy covers the claim and explains applicable benefits if accepted. 20

Pie’s agency FAQ says Pie manages workers’ compensation claims in 34 states and CorVel handles Alaska, Mississippi, Nevada, New Mexico and Oregon. That 39-state split is not reconciled with the separately advertised 40-state-plus-D.C. footprint. 21,11,22

Resilience describes a 24/7 in-house claims team, a dedicated claims manager through settlement, and outside specialists in privacy law, forensics, recovery and crisis communications. These are company-reported service arrangements, not independently measured claims quality. 31

Sources

Pie Insurance Official Website

  1. Pie Insurance. 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. Pie Insurance; About Pie; direct and agency distribution; footer legal disclosure. Accessed 2026-09-15.
  3. Workers’ Comp Insurance For Small Businesses. Pie Insurance; Quote inputs; coverage description; company-reported quote-time and savings qualifications; AM Best link. Accessed 2026-09-15.
  4. 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. Pie Insurance — Quote. Pie Insurance; Live unauthenticated first step: Business ZIP Code; inspected without entering data or advancing. Accessed 2026-09-15.
  6. Business Owner’s Policy. Pie Insurance; BOP definition; typical components; invitation to start a BOP quote; footer third-party insurer qualification. Accessed 2026-09-15.
  7. Cyber Insurance For Small Businesses. Pie Insurance; First- and third-party descriptions; carrier-partner quote invitation; policy-variation qualification. Accessed 2026-09-15.
  8. Errors And Omissions Insurance. Pie Insurance; E&O and professional-liability equivalence; typical claims; carrier-partner placement statement; footer third-party insurer qualification. Accessed 2026-09-15.
  9. General Liability Insurance. Pie Insurance; Typical covered categories; carrier-partner quote invitation; footer third-party insurer qualification. Accessed 2026-09-15.
  10. Workers’ Comp Coverage By State. 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.
  11. Agency Document Library. Pie Insurance; Workers’ Comp State Documents: 40 named states plus Washington, D.C.. Accessed 2026-09-15.
  12. Pie Insurance Reports Strong 2025. Pie Insurance; 13 January 2026 release; Key 2025 Milestones says 39 states plus Washington, D.C.; company and distribution description. Accessed 2026-09-15.
  13. Commercial Auto Claim FAQs. 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.
  14. 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.
  15. Workers’ Comp FAQs. Pie Insurance; Certificates; waiver request timing and state-dependent charge; billing and payments; renewal timing; annual audit; claims. Accessed 2026-09-15.
  16. 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.
  17. Pay-As-You-Go With Pie Insurance. Pie Insurance; No initial deposit; actual-payroll monthly premium; automatic deductions; payroll-provider coordination. Accessed 2026-09-15.
  18. Your 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.
  19. File Your Claim Within 24 Hours. Pie Insurance; Workers’ compensation reporting by online form, 24/7 phone or email; information requested; post-report coverage determination. Accessed 2026-09-15.
  20. Partner FAQ. Pie Insurance; Workers’ compensation claim handling in 34 states; CorVel handling in Alaska, Mississippi, Nevada, New Mexico and Oregon; producer commissions on earned premium. Accessed 2026-09-15.
  21. AM Best Rating Disclosure Report — Pie Casualty Insurance Company. 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.
  22. The Pie Insurance Company — Company Details. 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.
  23. Pie Casualty Insurance Company — Entity Details. Illinois Department of Insurance; Legal name; P&C Domestic Stock; active status; NAIC 10997; Pie Group Holdings, Inc. parent. Accessed 2026-09-15.
  24. Administrative Actions — January 2024. 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.

Resilience Official Website

  1. Home Page. Resilience; Cyber risk management; Broad market appetite. Accessed 2026-09-16.
  2. Disclaimer. Resilience; Opening paragraphs and USA jurisdiction disclosure. Accessed 2026-09-16.
  3. Cyber Insurance. Resilience; Why choose cyber insurance; Policy coverage; Broad market appetite. Accessed 2026-09-16.
  4. Technology E&O. Resilience; Technology risk categories; Key benefits / A Broad Market Appetite. Accessed 2026-09-16.
  5. Brokers. Resilience; Broker benefits; Use cases; Insurance & risk solutions. Accessed 2026-09-16.
  6. Claims & Incident Response. Resilience; Our difference; Support from start to resolution; Claims panel. Accessed 2026-09-16.
  7. Contact Us. Resilience; Contact us; emergency claims instructions. Accessed 2026-09-16.
  8. Security Investment Prioritization. Resilience; Resilience Edge introduction and Key benefits. Accessed 2026-09-16.
  9. Multi-Entity & Portfolio Risk. Resilience; Resilience Arc introduction. Accessed 2026-09-16.
  10. Terms and Conditions. Resilience; Opening website agreement; separate written agreements. Accessed 2026-09-16.

Updated . Spot, a product of Tools for Enlightenment, publishes this research and works in the commercial insurance market. Editorial policy. To suggest a correction, contact Spot with the page URL and supporting source.

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