Pie Insurance vs
The Hartford
How Pie’s workers’-compensation-first carrier group differs from The Hartford’s broader small-business and SaaS insurer catalogue.
Introduction
A contractor shopping workers’ compensation is comparing two insurance groups that both write that line, not a broker versus an insurer. Pie says it stopped writing new commercial-auto business. Hartford still markets commercial auto, but not on its small-business self-serve site. Neither workers’-compensation footprint is described as all states. 3 37
Where Each Provider Shines
Where Pie Insurance Shines
Where The Hartford Shines
- The Hartford designs small-business packages for SaaS and other software companies, typically starting from a business owner’s policy. 26,27,49,48
- Small-business buyers can start an online quote-and-buy flow or call, or use an independent Hartford agent; commercial auto is not sold on that self-serve path. 27,26,33,32,42,44
Coverage Comparison
| Coverage Type | Pie Insurance | The Hartford |
|---|---|---|
| Business owner’s policy | Listed 7 | Listed 34,26 |
| Commercial auto | Not listed | Listed 42,26 |
| Commercial property | Not listed | Listed 36,26 |
| Crime | Not listed | Listed 44 |
| Cyber liability | Listed 8 | Listed 38,26 |
| Directors and officers | Not listed | Listed 44,45 |
| Employee health and benefits | Not listed | Listed 49 |
| Employment practices liability | Not listed | Listed 41,26 |
| Fiduciary liability | Not listed | Listed 44 |
| General liability | Listed 10 | Listed 35,26 |
| Hired and non-owned auto | Not listed | Listed 43,42 |
| Kidnap and ransom | Not listed | Listed 44 |
| Management liability | Not listed | Listed 44 |
| Professional liability / E&O | Listed 9 | Listed 40 |
| Technology errors and omissions | Not listed | Listed 39,38 |
| Tools, equipment and inland marine | Not listed | Listed 48 |
| Umbrella and excess liability | Not listed | Listed 46,47 |
| Workers’ compensation | Listed 3 | Listed 37,26 |
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 the Hartford
Pie Carriers Versus Hartford Fire Group
Pie Group Holdings owns the site; Pie Insurance Services is the producer. Workers’ compensation is described as written by The Pie Insurance Company and Pie Casualty Insurance Company, with an AM Best A- pooled rating as of 24 April 2026. Partner products do not name current issuers for a business owner’s policy, general liability, professional liability or cyber on Pie’s published legal materials. 5 22
Hartford Fire Insurance Company (NAIC 19682) is listed as authorized in all states in Hartford’s legal notice and independently in California’s Department of Insurance profile. That still does not assign Hartford Fire to every product. 29 53
State Count and Monopolistic Markets
Pie’s WC state count conflicts between 39-plus-D.C. and 40-plus-D.C. messaging. Hartford says some states require a state-fund WC product that a private insurer cannot sell. Confirm locations before treating either brand as national WC. 3 37
Pie’s remaining published catalogue is workers’ compensation, a business owner’s policy, cyber, general liability and professional liability. Hartford also markets FailSafe, management-liability packages and employee benefits. Pie’s published product set is not presented as a technology-errors-and-omissions specialty. 7 39
Pay-As-You-Go Mechanics
Both describe pay-as-you-go WC. Pie publishes a 3% card fee on certain new single-state WC policies and a 16.6% plus ten-month installment option. Hartford describes pay-as-you-go against actual payroll without that Pie fee table. Annual premium audits can change the final number at either company. 3 37
What to Confirm in Quotes
Service Comparison
Pie Insurance vs The Hartford: documented services and availability
| Criteria | Pie Insurance | The Hartford |
|---|---|---|
| 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 | The Hartford is the brand of The Hartford Insurance Group, Inc., a financial holding company whose subsidiaries underwrite property-and-casualty insurance, employee benefits and other financial products. Independent agents and brokers, and Hartford employees who sell insurance, distribute those products. The brand is not itself the insurer on a policy. 29,50,46,32 |
| Coverage lines | 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. 3,7,8,10,9,4 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. 14,20 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. 4 | Documented Hartford offerings for businesses include a business owner’s policy (general liability, commercial property and business income), stand-alone general liability and commercial property, workers’ compensation, cyber (including BOP data-breach add-ons, CyberChoice First Response and FailSafe Technology E&O), miscellaneous professional liability, employment practices liability, commercial auto and hired/non-owned auto, management-liability packages (Private Choice Premier: directors and officers, EPL, fiduciary, crime, kidnap and ransom), commercial umbrella, employee benefits, and inland marine for midsize and large accounts. Actual forms, limits and availability vary by product, state and underwriting. 26,34,38,39,40,41,42,43,44,46,49,48 The Hartford’s employment-practices page states there is no built-in EPL coverage in California, Minnesota, North Dakota or New York, and that the EPL program described on that page does not apply to EPL coverage written in California. Coverages also vary by state and class. 41 |
| Availability | Pie’s dedicated state page and AM Best describe workers’ compensation in 40 states and Washington, D.C., but Pie’s homepage and January 2026 release say 39 states plus D.C. Confirm the business locations and class codes in the current quote or agent portal. 11,12,1,13,22 The reviewed BOP, cyber, general-liability and professional-liability pages do not publish a product-by-state availability table. Pie’s terms also say products are not available in every US area or situation. 7,8,10,9,4 | The Hartford states that products are not available in all states or for all businesses, and that listing a writing company as authorized to transact insurance does not guarantee that coverage will be offered. Workers’ compensation pages also say that in some states coverage can be bought only from a state-run program, not from a private insurer such as The Hartford. 27,29,37,34 The Hartford operates a California small-business insurance page that lists BOP, general liability, workers’ compensation, commercial auto, commercial property and professional liability and says California buyers can get a quote online or by phone. Hartford Fire Insurance Company is independently listed by the California Department of Insurance as an authorized property-and-casualty insurer (NAIC 19682). Those facts do not identify which affiliate would issue a particular California policy or whether a given SaaS risk will be accepted. 28,53,29 |
| 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 | The Hartford says eligible small-business buyers can get a free quote online in minutes or by phone, and can also buy through independent agents. Its public quote-and-buy portal shows steps from Basics through Payment and Confirmation. It also says buyers can purchase without an agent. Commercial auto for small businesses is not currently offered on that online path and may be quoted through a local agency or Tivly. Management-liability pages direct buyers to find a local agent. 27,26,33,32,42,44 |
| Fees and compensation | 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. 17,18 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. 17 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. 16 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. 21,5 | The Hartford discloses that it pays independent producers base commissions (a percentage of premium or a fixed amount per policy), and may also pay contingent or supplemental commissions, fees for services, delegated-underwriting compensation and other benefits. Employees who sell insurance may receive extra compensation beyond salary. Producers may charge their own customer fees that are not Hartford premium. The reviewed pages do not publish the commission rate or any Hartford-charged service fee that would apply to a particular buyer’s policy. Published “average premiums” are company-reported estimates, not quotes. 50,32,27,26 |
Sources
Pie Insurance Official Website
- Pie Insurance. Pie Insurance; Homepage: small-business audience; direct workers’ compensation quote; online account; footer entity, insurer and availability qualifications. Accessed 2026-09-15.
- About Pie Insurance. Pie Insurance; About Pie; direct and agency distribution; footer legal disclosure. Accessed 2026-09-15.
- 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.
- 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.
- Legal. Pie Insurance; State Licenses; footer disclosure naming producer and workers’ compensation versus third-party underwriting roles. Accessed 2026-09-15.
- Pie Insurance — Quote. Pie Insurance; Live unauthenticated first step: Business ZIP Code; inspected without entering data or advancing. Accessed 2026-09-15.
- 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.
- Cyber Insurance For Small Businesses. Pie Insurance; First- and third-party descriptions; carrier-partner quote invitation; policy-variation qualification. Accessed 2026-09-15.
- 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.
- General Liability Insurance. Pie Insurance; Typical covered categories; carrier-partner quote invitation; footer third-party insurer qualification. Accessed 2026-09-15.
- 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.
- Agency Document Library. Pie Insurance; Workers’ Comp State Documents: 40 named states plus Washington, D.C.. Accessed 2026-09-15.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
The Hartford Official Website
- SaaS Insurance for Your Business. The Hartford; Audience list (software startups, SaaS, IT consulting); BOP contents; add-ons (workers’ compensation, data breach, commercial auto); cyber, EPLI, technology professional liability mentions; online quote claim; company-reported industry-average premiums footnote. Accessed 2026-09-16.
- Small Business Insurance | Get a Quote. The Hartford; Small-business positioning; BOP package; product list including professional liability, cyber, EPLI, commercial auto; quote in minutes and COI 24/7; phone 855-487-0783; availability footnote that products are not available in all states or for all businesses. Accessed 2026-09-16.
- California Business Insurance. The Hartford; Coverages marketed for California (BOP, general liability, workers’ compensation, commercial auto, commercial property, professional liability); statement that California buyers can get a quote online or by phone; company-reported California customer averages. Accessed 2026-09-16.
- Legal Notice. The Hartford; The Hartford Insurance Group, Inc. holding-company description; no representation that all products are available in all locations; P&C writing-company table as of December 31, 2025 including Hartford Fire (NAIC 19682) and Hartford Underwriters (NAIC 30104); life writing companies including Hartford Life and Accident (NAIC 70815). Accessed 2026-09-16.
- The Hartford Announces First Quarter 2025 Financial Results. The Hartford; Boilerplate: The Hartford Insurance Group, Inc. (formerly Hartford Financial Services Group, Inc.), NYSE: HIG, operates through subsidiaries under the brand The Hartford, headquartered in Hartford, Connecticut. Accessed 2026-09-16.
- About Us. The Hartford; Property and casualty insurance, group benefits and mutual funds positioning; more than 200 years of operation. Accessed 2026-09-16.
- Find a Local Insurance Agent. The Hartford; Small-business and midsize agent locators; FAQ that buyers can purchase without an agent by calling or quoting online; statement that agents may charge fees. Accessed 2026-09-16.
- Small Business Insurance Quote. The Hartford; Public first screen: business-status and structure questions; steps labeled Basics, Coverages, Details, Price, Review, Payment and Confirmation; help phone 1-855-431-1252 (M–F 8am–8pm ET). Viewed without submitting an application. Accessed 2026-09-16.
- Business Owner’s Policy (BOP) Insurance. The Hartford; BOP contents (property, general liability, business income); optional add-ons including workers’ compensation, professional liability, commercial auto and cyber; last updated May 20, 2026; products-not-available-in-all-states footnote. Accessed 2026-09-16.
- General Liability Insurance. The Hartford; Stand-alone GL and BOP bundling; products-completed operations; technology-company example; last updated May 20, 2026; subsidiary-offering disclosure referencing the Legal Notice. Accessed 2026-09-16.
- Commercial Property Insurance. The Hartford; Property and business-interruption descriptions; technology firms listed among common buyers; COI online; claims phone 800-327-3638; last updated August 13, 2025. Accessed 2026-09-16.
- Workers' Compensation Insurance Plans. The Hartford; State-requirement quiz noting some states require purchase from a state-run program rather than a private insurer; pay-as-you-go billing; My Workers’ Comp Connection portal; provider-network and pharmacy statements. Accessed 2026-09-16.
- Cyber Insurance for Small Businesses. The Hartford; BOP-endorsed cyber versus CyberChoice First Response versus FailSafe Technology E&O; Cyber Center; FirstResponse hotline 800-370-0605; last updated March 10, 2026. Accessed 2026-09-16.
- Technology Errors and Omissions Insurance | Technology E&O. The Hartford; FailSafe Technology Liability Product Suite features including E&O, security, data privacy/network security, personal injury, intellectual property and media liability; software and SaaS-relevant buyer classes; last updated September 19, 2024. Accessed 2026-09-16.
- Professional Liability Insurance Coverage. The Hartford; Miscellaneous professional liability and a listed Errors & Omissions Insurance for Technology Companies product; claims-made versus occurrence discussion; My Account COI requests; last updated May 4, 2026. Accessed 2026-09-16.
- Employment Practices Liability Insurance | EPL Insurance. The Hartford; Hartford-provided EPLI; BOP inclusion claim; Private Choice Premier and Employers Premier Choice; footnotes that built-in EPL coverage is not available in California, Minnesota, North Dakota or New York and that the described EPL program does not apply to EPL written in California; last updated November 26, 2025. Accessed 2026-09-16.
- Commercial Auto Insurance Coverage. The Hartford; Statement that The Hartford does not currently offer this coverage online for small businesses and may route quotes through a local agency or Tivly; hired and non-owned auto description; last updated August 27, 2026. Accessed 2026-09-16.
- Hired and Non-Owned Vehicle Insurance | HNOA. The Hartford; Hartford offering of hired and non-owned auto; liability-only limitations; last updated August 27, 2026. Accessed 2026-09-16.
- Management Liability Insurance | Get a Quote. The Hartford; Private Choice Premier package (D&O, EPL, fiduciary, crime, kidnap and ransom/extortion); option to add certain coverages to a BOP; instruction to find a local agent. Accessed 2026-09-16.
- Directors and Officers Liability Insurance. The Hartford; Agent-facing D&O solutions for public companies, financial institutions, and private or nonprofit organizations via Private Choice Premier. Accessed 2026-09-16.
- Commercial Insurance. The Hartford; Insurer self-description; optional commercial umbrella; about-10-minute quote claim; products not available in all states; coverages may be offered by one or more P&C subsidiaries listed in the Legal Notice. Accessed 2026-09-16.
- Business Insurance Coverage. The Hartford; Commercial umbrella, EPL, data breach and other coverage descriptions; last updated July 28, 2025; products-not-available-in-all-states footnote. Accessed 2026-09-16.
- Inland Marine Insurance Solutions. The Hartford; Midsize and large inland-marine programs including technology equipment; Quick Quote submissions; premium-start statement for larger businesses. Accessed 2026-09-16.
- Employee Benefits Insurance. The Hartford; Employer income-protection and related benefits; footer naming Hartford Life and Accident Insurance Company and Hartford Fire Insurance Company as underwriting companies. Accessed 2026-09-16.
- Producer Compensation Property & Casualty. The Hartford; Distribution through agents and brokers; base, contingent and supplemental commissions; employee sales compensation; surplus-lines brokers; producer-charged customer fees that are not Hartford premium. Accessed 2026-09-16.
- Insurance Claim Center. The Hartford; Phone and online reporting; online claim status; mobile app for claims, policy details and billing. Accessed 2026-09-16.
- General Liability Claims | File A Claim. The Hartford; 24/7 phone 800-327-3636; online general-liability claim form; policy-type selector including cyber, employee benefits, property and workers’ compensation. Accessed 2026-09-16.
- Hartford Fire Insurance Company. California Department of Insurance; NAIC 19682; California Company ID 0085-1; authorized 01/07/1870; license status UNLIMITED-NORMAL; property and casualty; domicile Connecticut; authorized lines including liability, fire, workers’ compensation, automobile, surety and marine. Accessed 2026-09-16.
Suggested Comparisons
Alliance Risk vs Pie Insurance
Alliance Risk and Pie Insurance compared for a growing employer separating workers’ compensation cash flow from its wider insurance program.
Alliance Risk vs The Hartford
How Alliance Risk’s independent technology brokerage, with conflicting state-availability language, differs from The Hartford as insurer.
Amelia Risk vs Pie Insurance
Compare workers-compensation purchasing and payroll administration with a broker coordinating a broader product-company program.





