Chubb vs Pie Insurance

Compare Chubb’s small-commercial workers’ compensation and packages with Pie Insurance’s worker-comp-first digital program and partner-carrier add-ons.

Introduction

A five-person SaaS company that mainly needs workers’ compensation can start a Pie quote online. The same company that also needs DigiTech and D&O still needs other paper—Pie’s partner products or a Chubb (or other) agent. Pie is not a replacement for Chubb’s technology liability catalogue. 46 10

Where Each Provider Shines

Where Chubb Shines

  • DigiTech ERM packages technology E&O, media and cyber on one Chubb policy for software, services and hardware companies. 10,9,4
  • Appointed agents quote eligible small-commercial and cyber accounts in Chubb Marketplace, with Cyber Central for express cyber quoting. 9,10,30,31,12

Where Pie Insurance Shines

  • Small businesses can start a workers’ compensation quote directly online or through an insurance agent. 45,44,46
  • Workers’ compensation payment options include pay-as-you-go using reported payroll, with no initial deposit. 60,61

Coverage Comparison

Coverage TypeChubbPie Insurance
Builders riskListed 22,21Not listed
Business owner’s policyListed 7,4Listed 50
Cargo and transitListed 24Not listed
Commercial autoListed 17,7Not listed
Commercial propertyListed 15,4Not listed
CrimeListed 11,5Not listed
Cyber liabilityListed 10,9Listed 51
Directors and officersListed 13,11Not listed
Employment practices liabilityListed 11,14Not listed
Equipment breakdownListed 23,5Not listed
Fiduciary liabilityListed 11,14Not listed
General liabilityListed 7,4,20Listed 53
Kidnap and ransomListed 11,14Not listed
Management liabilityListed 11,14Not listed
Media liabilityListed 10Not listed
Product recallListed 26,28Not listed
Professional liability / E&OListed 10,5Listed 52
Representations and warrantiesListed 27Not listed
Surety bondsListed 25Not listed
Technology errors and omissionsListed 10,4Not listed
Tools, equipment and inland marineListed 21,28Not listed
Umbrella and excess liabilityListed 16,7Not listed
Workers’ compensationListed 8,4Listed 46

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 Chubb and Pie Insurance

Workers’ Comp Specialist Versus Multi-Line Group

Pie Insurance Services sells and administers small-business commercial policies; affiliated carriers write workers’ compensation and some other lines come through outside partners. Chubb is a marketing name for group underwriting companies that issue their own commercial lines, including workers’ compensation as a Chubb product. 48 46 2

Pie names The Pie Insurance Company and Pie Casualty Insurance Company as workers’ compensation underwriters. Chubb names Federal Insurance Company among primary underwriting companies. Those are different balance sheets. 48 30

Direct Quote Versus Agent Marketplace

Pie offers a public workers’ compensation quote flow and an agency channel. Chubb’s small-business workers’ compensation is described as combinable with a Chubb businessowners policy and is sold through appointed agents. Pie’s statements about quote time and savings are Pie’s own, with qualifications on those pages. 49 8

Partner Lines and Auto Discontinuance

Pie’s public catalogue still supports businessowners, cyber, general liability and professional liability requests through partners, with less public insurer detail than its workers’ compensation companies. Its FAQ says new commercial auto submissions and renewals ended. Chubb still markets commercial auto as a company product. Pie partner cyber or professional liability is not shown here as Chubb DigiTech wording. 51 57 17

Cost Features Pie Publishes

Pie discloses payment plans, a credit-card fee on many new single-state workers’ compensation policies, and charges for waiver-of-subrogation requests without a public dollar schedule. Chubb does not publish comparable buyer fee tables. Payroll audits on Pie workers’ compensation can change premium after the term. 60 62 29

What to Confirm in Quotes

  • Workers’ compensation issuer: Pie-group companies versus a Chubb-group company, plus AM Best or other rating needs. 65 30

  • State availability, including Pie’s conflicting public state counts. 54 2

  • Whether BOP, cyber or E&O on a Pie proposal uses partner paper rather than Pie’s workers’ comp companies. 48

  • Credit-card, waiver and audit terms versus a Chubb WC quote’s payment method. 60 8

Service Comparison

Chubb vs Pie Insurance: documented services and availability

CriteriaChubbPie Insurance
Business role

Chubb is the marketing name for subsidiaries of Chubb Limited, a Swiss holding company, that provide insurance and related services. U.S. commercial policies are issued by U.S.-based Chubb underwriting companies, not by Chubb Limited itself. 39,2,25

Commercial buyers typically reach Chubb through independent agents and brokers. Chubb appoints producers, operates agent portals, and identifies Chubb Insurance Solutions Agency, Inc. as the licensed agency that administers Chubb Access appointments. Surplus-lines products can be offered only through licensed surplus-lines producers. 29,30,2,38

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. 45,48,46,50,51,52,53

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. 47,67,65

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. 48,68

Coverage lines

For technology companies, Chubb markets DigiTech Enterprise Risk Management as a single policy addressing technology errors and omissions, media and cyber exposures, alongside Cyber ERM for cyber, privacy and media and Pro ERM for professional, media and cyber. Actual terms, limits and exclusions are in the issued form. 10,9,4

Chubb’s U.S. commercial catalogue for technology and other businesses also includes package policies (BOP, Benchmarq and Customarq combining property, business income and general liability), workers’ compensation, commercial auto, umbrella and excess, ForeFront management-liability parts (including D&O, employment practices, fiduciary and crime), property, inland marine, builders’ risk, equipment breakdown, ocean cargo, environmental/pollution, surety, product recall, and representations and warranties for large-account multinational programs. 4,7,11,15,25,27

Current direct offering pages support workers’ compensation, business owner’s policy, cyber, general liability and professional liability/E&O. The non-workers’ compensation pages describe typical protection; the issued policy and endorsements determine actual coverage. 46,50,51,53,52,47

Pie says it stopped accepting commercial-auto submissions on December 1, 2025 and will issue no new or renewal commercial-auto policies on or after January 1, 2026. Existing policyholders retain coverage through their policy term and can still use Pie’s claim channels. 57,63

Pie’s terms say website coverage descriptions are not part of an insurance contract and do not change a policy or endorsement; eligibility and product availability can vary by geography and applicant. 47

Application process

Appointed agents and brokers can quote, and for eligible risks issue, small-business and cyber accounts through Chubb Marketplace, and can use Cyber Central for an express cyber quoting path. Marketplace cyber quoting is described for eligible risks with less than $100 million in revenue; referred risks go to underwriters. Businesses seeking coverage are directed to an agent, a U.S. contact form, or chubbsmallbusiness.com for small-business quote inquiries. The reviewed public pages do not describe a general-public online bind for middle-market technology programs. 9,10,30,31,12

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. 45,44,46

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. 49,46

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. 46,44

Access to insurers

The issuing insurer is a Chubb-group underwriting company named on the policy. Reviewed sources identify Federal Insurance Company as a primary U.S. underwriting company, ACE American Insurance Company as a U.S. issuing company on surety materials, and Westchester Fire Insurance Company or Westchester Surplus Lines Insurance Company (and, for some Westchester business, Illinois Union or other ACE paper) depending on the placement. Buyers should read the declarations rather than assume a single “Chubb” legal insurer. 30,25,28,36,41

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. 48,65,66,67

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. 65

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. 48,50,51,52,53

Fees and compensation

Reviewed buyer-facing U.S. pages do not publish premiums, producer-compensation schedules, or policyholder fees. Agent-recruiting copy refers to competitive commissions without stating rates. Inland marine engineering beyond included loss-control is described as available on a fee-for-service basis. 29,7,10,21

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. 60,61

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. 60

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. 59

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. 64,48

Sources

Chubb Official Website

  1. Insurance For Individuals & Businesses. Chubb; Businesses; Get a quote; claims statistics; insurance products and client services. Accessed 2026-09-16.
  2. Terms Of Use. Chubb; Acceptance of Terms identifying Chubb Group Holdings Inc.; surplus-lines producer restriction; products not available to all users or jurisdictions; Chubb Limited safe-harbor language; Internet Portals for Chubb Business. Accessed 2026-09-16.
  3. Commercial Insurance. Chubb; Industry practices; small businesses, middle market, large and multinational segments; claims paid and satisfaction figures. Accessed 2026-09-16.
  4. Insurance For Technology Companies. Chubb; Industry overview; who we serve; listed products including Package, E&O/Cyber, Financial Lines, workers’ compensation, auto, umbrella, BOP, Benchmarq and Customarq; dedicated underwriting, claims and risk engineering. Accessed 2026-09-16.
  5. Insurance For Software Product & System Developers. Chubb; Property & casualty and financial-lines coverage solutions lists for software and systems developers. Accessed 2026-09-16.
  6. Technology Services And Consulting Insurance Solutions. Chubb; Property & casualty and financial-lines coverage solutions lists. Accessed 2026-09-16.
  7. Business Owner’s Policy (BOP) Insurance. Chubb; Eligibility up to $30M revenue and 500+ classes including technology; property and liability package; supporting umbrella, workers’ compensation, commercial auto, ForeFront and Cyber ERM/DigiTech ERM. Accessed 2026-09-16.
  8. Workers' Compensation Insurance For Small Business. Chubb; Small-business workers’ compensation for one employee through $30M revenue; claims-service descriptions; supporting products. Accessed 2026-09-16.
  9. Cyber Insurance For Businesses. Chubb; Agent quoting via Chubb Marketplace and Cyber Central; policyholder incident-response hotline and Cyber Alert app; businesses seeking coverage directed to tailored protection rather than a public bind flow. Accessed 2026-09-16.
  10. Cyber Insurance Coverage & Products. Chubb; Cyber ERM, DigiTech ERM and Pro ERM product descriptions; Marketplace quoting for eligible risks under $100 million revenue; first- and third-party coverage summaries. Accessed 2026-09-16.
  11. The ForeFront Portfolio. Chubb; Available coverages for private, not-for-profit and healthcare organizations: D&O, EPL, fiduciary, employed lawyers, crime, kidnap/ransom and workplace violence expense. Accessed 2026-09-16.
  12. ForeFront Portfolio 3.0 For Private Companies. Chubb; Coverage highlights for private companies; contact-an-agent quote prompt; New Jersey application note. Accessed 2026-09-16.
  13. ForeFront Portfolio 3.0: Directors & Officers And Entity Liability Insurance. Chubb; Private-company D&O and entity liability description and listed coverage features. Accessed 2026-09-16.
  14. Management Liability Insurance. Chubb; Public, private/not-for-profit and financial-institution management liability products; fiduciary, crime, kidnap/ransom, workplace violence and employment practices. Accessed 2026-09-16.
  15. Commercial Property Insurance. Chubb; Monoline, multi-line and large/complex property offerings; technology listed among served industries; Risk Consulting. Accessed 2026-09-16.
  16. Umbrella & Excess Casualty Insurance. Chubb; Umbrella and excess for smaller through multinational accounts; Express Umbrella portal for appointed brokers. Accessed 2026-09-16.
  17. Commercial Auto Insurance. Chubb; Commercial auto product; technology among served industries. Accessed 2026-09-16.
  18. Customarq Package Insurance Policy. Chubb; Midsize package combining property and liability; supporting excess, cyber, cargo, workers’ compensation and commercial auto. Accessed 2026-09-16.
  19. Lower Midmarket Insurance Solutions. Chubb; Agent-facing lower-midmarket suite including Benchmarq package, financial lines, cyber on Marketplace, surety; technology among appetite SIC codes; quoting through issuance, servicing and renewals. Accessed 2026-09-16.
  20. Environmental Insurance Coverage & Services. Chubb; Premises and contractor pollution, TankSafe, GL Plus combining CGL with products and premises pollution and supported umbrella. Accessed 2026-09-16.
  21. Inland Marine Insurance. Chubb; Inland marine policy overview; builders’ risk, contractors equipment and related tools. Accessed 2026-09-16.
  22. Builders' Risk Insurance. Chubb; Builders’ risk coverage list and target clients; agent submission requirements. Accessed 2026-09-16.
  23. Equipment Breakdown Insurance. Chubb; Monoline and package equipment-breakdown coverage; electronics among target clients. Accessed 2026-09-16.
  24. Worldwide Ocean Cargo Insurance. Chubb; Ocean, air and overland cargo coverages; agent submission path. Accessed 2026-09-16.
  25. Surety Bonds. Chubb; Construction, commercial, transactional and international surety; footer identifying Chubb as marketing name and ACE American as an issuing company; products may not be available in all states. Accessed 2026-09-16.
  26. Chubb Recall Plus For Consumer Goods. Chubb; Product-recall offering, limits, restricted classes and electronics among target finished products. Accessed 2026-09-16.
  27. Multinational Insurance Coverage And Solutions For Large Accounts. Chubb; Core and specialty coverages including representations and warranties, inland marine, professional liability and ESIS; Worldview servicing platform; work with clients and brokers. Accessed 2026-09-16.
  28. Excess And Surplus Insurance (E&S Insurance). Chubb; Westchester E&S portfolio; Westchester Fire admitted description; Westchester Surplus Lines eligible in 49 states; paper including Illinois Union and ACE companies. Accessed 2026-09-16.
  29. Get Access To Chubb. Chubb; Direct appointments for independent agents and brokers; competitive commissions; 200+ products. Accessed 2026-09-16.
  30. Contact Chubb. Chubb; Agent as first contact; claims numbers including cyber; Small Business policy service and Marketplace technical support; Federal Insurance Company and ACE American claims contacts. Accessed 2026-09-16.
  31. Chubb Insurance In The U.S.. Chubb; Personal Lines find-an-agent; Small Business quote inquiries directed to chubbsmallbusiness.com; commercial agent callback 1-800-682-4822. Accessed 2026-09-16.
  32. Chubb Claims. Chubb; 24/7 claims contact center; company-reported satisfaction of clients with a paid claim; North America claims staffing figure. Accessed 2026-09-16.
  33. Report A Claim. Chubb; Phone and email first-notice contacts including small commercial, cyber, financial lines and workers’ compensation. Accessed 2026-09-16.
  34. Online & Mobile Claims Tools. Chubb; Small Commercial Business client portal claim reporting and document upload; access may be limited for policies underwritten by certain Chubb companies. Accessed 2026-09-16.
  35. About Chubb In The U.S.. Chubb; U.S. executive leadership and 44 branch locations; branch presence is not product-availability evidence. Accessed 2026-09-16.
  36. Chubb Company License Information. Chubb; Federal Insurance Company (Indiana NAIC 20281) admitted P&C in all 50 states; ACE American (Pennsylvania NAIC 22667) admitted P&C in all 50 states; Westchester Surplus Lines Insurance Company eligible/approved surplus lines outside Georgia domicile. Accessed 2026-09-16.
  37. Chubb Insurance Solutions Agency License Information. Chubb; Statement that Chubb Insurance Solutions Agency is licensed in all 50 states; resident NJ license 2853751; California license 969601. Accessed 2026-09-16.
  38. Chubb New York Region Appointment Materials. Chubb; Chubb Access appointments administered by Chubb Insurance Solutions Agency, Inc.; surplus lines sold only through licensed surplus lines producers; products may not be available in all states. Accessed 2026-09-16.
  39. Chubb Limited Form 10-K For The Year Ended 31 December 2025. U.S. Securities and Exchange Commission / Chubb Limited; Item 1 Business: Swiss-incorporated holding company headquartered in Zurich; global insurance and reinsurance organization; operations in 54 countries and territories; commercial P&C including D&O and specialty casualty. Accessed 2026-09-16.
  40. Chubb Limited Exhibit 21.1 Subsidiaries. U.S. Securities and Exchange Commission / Chubb Limited; ACE American Insurance Company; Federal Insurance Company group companies; Chubb Excess and Surplus Insurance Services Inc. (California); Chubb INA Holdings LLC. Accessed 2026-09-16.
  41. California Company Profile: Federal Insurance Company. California Department of Insurance; NAIC 20281; California Company ID 0059-6; date authorized 12/18/1902; license status Unlimited-Normal; company type Property & Casualty; domicile Indiana; NAIC Group 0626 Chubb Ltd Grp. Accessed 2026-09-16.
  42. California Company Profile: ACE American Insurance Company. California Department of Insurance; NAIC 22667; California Company ID 1325-0; date authorized 12/20/1945; license status Unlimited-Normal; company type Property & Casualty; domicile Pennsylvania; NAIC Group 0626 Chubb Ltd Grp. Accessed 2026-09-16.
  43. California NAIC Group List: Chubb Ltd Grp 0626. California Department of Insurance; Group roster including Federal Insurance Company, ACE American Insurance Company, Chubb National Insurance Company, Westchester Fire Insurance Company and other Chubb-group companies with California IDs. Accessed 2026-09-16.

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.

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.

Suggested Comparisons

All Comparisons

Let Spot Handle the Insurance Legwork.

Get help buying coverage and managing renewals, with less paperwork for your team. Start with a free consultation.

Talk to Spot