Pie Insurance vs RiskCube

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

RiskCube offers startup insurance brokerage through RiskCube Insurance Services, LLC. Its parent, RiskCube, Inc., supplies the platform and operational support; third-party insurers issue coverage. ^29,28

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

RiskCube says it compares multiple insurers. Its terms permit placements through surplus-lines channels; the reviewed legal disclosures and catalogue do not identify the issuing insurer for a specific California applicant. ^26,29,28,30

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

RiskCube describes one digital intake followed by AI-assisted and broker-reviewed quote comparison and digital purchase. The public application URL reviewed displayed a contact form rather than a complete underwriting flow. ^26,36

For technology E&O, RiskCube asks for product, customer, revenue and contract details, plus prior claims or known incidents. It qualifies its advertised quote timing by risk profile and underwriting complexity. ³²

RiskCube’s terms say quotes are not binders: written confirmation from the insurer or its authorized representative and required conditions must be satisfied before coverage is bound. ²⁹

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

RiskCube describes platform access for policy management, certificate generation and renewal notifications. A certificate does not change coverage under its terms. ^26,29

RiskCube says it reviews vendor insurance requirements and checks requested endorsements, including additional insured and waiver-of-subrogation language. Its terms warn that AI-assisted output can be incomplete or inaccurate. ^31,29

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

RiskCube’s homepage and FAQ advertise no added broker fees, but its compensation disclosure allows agreed service fees and payment-processing charges. It also describes insurer or intermediary commissions and possible performance incentives. The scope of the fee-free claim needs written clarification for the requested services. ^26,31,28