Frank Winston Crum Insurance

What Frank Winston Crum Insurance does

Frank Winston Crum Insurance (FWCI) is a commercial insurance carrier founded in 2003 and headquartered in Clearwater, Florida. The company operates a dual structure combining an AM Best B++ rated insurance carrier with a managing general agency (MGA) that holds underwriting authority for A-rated carrier partners ClearBlue Insurance Group and Benchmark Insurance Company. FWCI's product portfolio is anchored by workers' compensation insurance (currently offered in 38 states plus Washington D.C. across 350+ class codes) and includes Contractor Coverage Solutions, Commercial Package Policy (launched January 2026), Professional Employer Organization (PEO) bundling via its FrankCrum PEO affiliate, and stand-alone general liability and excess liability. The carrier is positioned for small businesses and the contractor/trades vertical with a stated appetite for risks other carriers decline, including start-ups, lapsed coverage, and accounts with no prior coverage, and operates a Florida-only workers' compensation dividend plan.

Distribution is exclusively indirect: FWCI's products are sold through a curated network of independent insurance agents using its proprietary Winston online platform, which supports two-minute quoting, five-minute binding for pre-approved risks, integrated underwriting referrals, one-click rewrites, and a flexible Winston PayGo payment option. Internal technology and operational functions are supported by a partner ecosystem that includes Majesco for policy and billing (phased rollout beginning summer 2024), Ivans Download for agency management system data exchange, TrustedChoice.com for agent digital marketing, and claims-side partners CCMSI (claims administration), Optum (pharmacy benefits management), TalisPoint (provider network search), and Job Fit (return-to-work programs).

FWCI is privately held by the Crum family within the broader FrankCrum enterprise, which also includes FrankCrum Staffing and FrankCrum PEO. The company reported $105.31 million in revenue for FY2024 (up 98% from 2021), holds 74,000+ policies in force, and operates with 154 FTEs (as part of a 400+ employee FrankCrum enterprise). Matt Crum serves as President (since 2013); Frank W. Crum Jr. remains owner, founder, and Chairman. Leadership was further deepened with the appointments of Scott Mackey as Chief Underwriting Officer, Hector Cano as VP of Workers' Compensation Claims, George Schwab as VP of Operations, and Michael Webb as enterprise CISO/SVP of IT Operations. Certification and recognition signals include AM Best B++ (Positive outlook), 2025 Inc. 5000 (#61 in insurance), 2026 USA TODAY Top Workplace, and 16 consecutive Tampa Bay Times Top Workplace awards.

Name

Frank Winston Crum Insurance

Legal name

Frank Winston Crum Insurance Company

Website

https://fwcruminsurance.com

Company type

Private

Founded year

2003

Operating status

Operating

Headcount range

51–100 employees

Short description

Frank Winston Crum Insurance is a privately held commercial insurance carrier and MGA, founded in 2003 and headquartered in Clearwater, Florida, underwriting workers' compensation, contractor coverage, and a new Commercial Package Policy for small businesses through a curated network of independent agents.

Ownership category

akta.pro rank

Product category

Commercial Insurance (Workers' Compensation & Liability)

NAICS

Direct Insurance (except Life, Health, and Medical) Carriers (52412), Insurance Agencies and Brokerages (524210), Insurance Agencies and Brokerages (52421)

SIC

Insurance Agents, Brokers & Service (6411)

akta.pro primary industry

Insurance Program Administration & MGA/MGU Services (FSAEADAK)

Keywords

• Workers compensation insurance
• Commercial insurance carrier
• Managing general agency
• Commercial package policy
• Independent agent distribution

Headquarters

HQ city

Clearwater

HQ country

United States

HQ region

North America

Offices1 record

Markets served

GTM type

B2B

Offering type

Services

Cost components

Operations, Personnel, Technology or R&D, Marketing or Sales, Infrastructure

Revenue model

1. Workers' Compensation Insurance: FWCI directly underwrites workers' compensation policies, covering medical benefits and wage replacement for employees who get injured or ill on the job, protecting the business from financial loss.
2. General Liability Insurance: Commercial general liability coverage for contractors, tradespeople, and small businesses, bundling essential coverages into comprehensive policies.
3. Commercial Package Policy (CPP): Bundles essential coverages including General Liability, Business Personal Property, Business Income, Crime & Fidelity, and Inland Marine into a single customizable policy.
4. Contractor Coverage Solutions: Business coverages tailored to contractors and tradespeople including GL, Excess Liability, Inland Marine, and WC in select states.
5. PEO Workers' Compensation: Workers' compensation coverage bundled with business services through FrankCrum PEO relationship, including HR, payroll, benefits, and compliance support.
6. Excess Liability: Excess liability coverage available automatically for qualifying GL policies with $1M, $2M, $3M, and $4M limits.

Pricing tiers

Go-to-market motion2 records

Distribution channels3 records

Marketing channels5 records

Core offering

Frank Winston Crum Insurance operates as a dual-structure commercial insurance carrier and managing general agency (MGA) that underwrites workers' compensation, contractor coverage solutions, commercial package policies, and PEO-bundled coverage. Products are distributed exclusively through a curated network of independent insurance agents who use the proprietary Winston online platform for quoting, binding, and policy servicing.

Product overview

Frank Winston Crum Insurance operates as a dual-structure commercial insurance carrier and managing general agency (MGA), offering a portfolio of workers' compensation, contractor coverage, and commercial package policy products. The company provides its coverage through an exclusive network of independent agents using the Winston digital platform for quoting and policy servicing. Frank Winston Crum Insurance (FWCI) directly underwrites policies as an AM Best B++ rated carrier, while the MGA operation provides access to additional A-rated carrier partners including ClearBlue Insurance Group and Benchmark Insurance Company.

Differentiator

Problem solved

Functional benefit

Brands

• Winston: Online quoting and policy-servicing portal for agents

Products and services

• Workers' Compensation Covers medical benefits and wage replacement for employees who get injured or ill on the job, protecting businesses from financial loss. Offered in 38 states and DC across 350+ class codes.
• Contractor Coverage Solutions Business coverages tailored to the needs of contractors and tradespeople, including General Liability, Excess Liability, Inland Marine, and Workers' Compensation in select states.
• Commercial Package Policy (CPP) Bundles essential coverages including General Liability, Business Personal Property, Business Income, Crime & Fidelity, and Inland Marine into a single comprehensive policy for small businesses.
• Professional Employer Organization (PEO) Provides a suite of solutions for businesses including workers' compensation coverage, HR support, payroll, employee benefits, and more through the FrankCrum PEO affiliation.

Quantifiable outcome

• Over 74,000 policies in force
• +2 more outcomes

Named customers1 record

Segments4 records

Ideal customer profiles3 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Integration1 record

AI capability2 records

Feature3 records

Partnerships

Six partnerships are on record, tiered core.

• MajescocoreTechnology or Integration · 20 May 2024FWCI partnered with Majesco, a leading global cloud insurance platform and commercial insurance software company, to complete a large-scale business transformation project with phased rollout starting summer 2024. The selection of Majesco's solutions supports FWCI's growth plans for current lines of business and will accelerate bringing new products to market quickly. Majesco Policy and Billing for P&C empowers customers to optimize operations, enhance customer experiences, and drive growth and profitability.
• TrustedChoice.comcoreGTM or Marketing Partner · 1 November 2022FWCI partnered with TrustedChoice.com, a leading marketing platform for independent agents, to expand its digital footprint and promote its network of agency partners. The mission of TrustedChoice.com is to help insurance consumers easily connect with independent insurance agents. FWCI joined its ecosystem to increase visibility and support agents, who receive boosted placement in search results and promotion as recommended agencies.
• Ivans DownloadcoreTechnology or Integration · 25 October 2022FWCI policy data is now available through Ivans Download, which automates the exchange of individual information requests via a single end-to-end application providing connectivity to agency distribution channels. This enables the most up-to-date information to be available from underwriting through to servicing directly in agency partners' management systems.
• CCMSIcoreTechnology or IntegrationCCMSI serves as FWCI's claims adjustment partner, assigning claims adjusters to contact policyholders and injured workers within 24 hours of claim filing. Adjusters act as gatekeepers investigating compensability, administering benefits, overseeing adjudication, and working closely with FWCI's claims management team.
• ClearBlue Insurance GroupcoreTechnology or IntegrationThrough FWCI's MGA structure, agents have access to ClearBlue Insurance Group (A-rated) coverage options for clients requiring higher ratings for bonding or contract requirements. FWCI's managing general agency has underwriting authority for ClearBlue alongside its own carrier.
• Benchmark Insurance CompanycoreTechnology or IntegrationThrough FWCI's MGA structure, agents have access to Benchmark Insurance Company (A-rated) coverage options for clients requiring higher ratings for bonding or contract requirements. FWCI's managing general agency has underwriting authority for Benchmark alongside its own carrier.

Scale indicators6 records

Recent moves9 records

Expansion highlights6 records

Direct peers

• Employers Holdings: Direct workers' compensation carrier focused on small businesses through independent agents. Closely comparable in product mix (WC as core), distribution (agent-led), and target customer (sub-50-employee employers).
• AmTrust Financial Services: Specialty P&C carrier with a strong workers' comp franchise and significant small-business and contractor book. Comparable on product mix (WC + GL), SME focus, and agent distribution model.
• ICW Group: Workers' compensation-focused carrier serving small and mid-sized businesses through independent agents. Closely aligned in line-of-business emphasis and distribution model.
• Zenith Insurance Company: Workers' comp specialist carrier with significant small-business exposure and agent distribution. Comparable in core line, customer segment, and rating tier ambitions.
• Accident Fund Holdings: Workers' compensation carrier with multi-state footprint serving small and mid-sized employers through agents. Direct competitor in the same WC product category.
• FCCI Insurance Group: Commercial P&C carrier focused on small to mid-sized businesses across WC, GL, and commercial package policies. Comparable on multi-line P&C offering for small businesses via independent agents.
• Builders & Tradesmen's Insurance Services: Workers' comp and commercial insurance provider specialized for contractors and tradespeople. Closely comparable in vertical focus (contractor coverage solutions) and SMB distribution.
• EMC Insurance Companies: Workers' comp and commercial P&C carrier serving small and mid-sized businesses through independent agents. Comparable on product portfolio and agency-led GTM.

Broad incumbents

• The Hanover Insurance Group: National P&C carrier with small-commercial and workers' comp capability through independent agents. Larger, broader-line incumbent that overlaps with FWCI's small-business commercial book.
• Main Street America Insurance: National small-commercial P&C carrier distributed through independent agents. Overlaps with FWCI's CPP and small main street business segments at a larger scale.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat6 records

Key risks7 records

Key highlights7 records

Customer concentration

• YouTubeyoutube.com/@frankcrum
• Facebookfacebook.com/FrankWinstonCrumInsurance
• LinkedInlinkedin.com/company/frank-winston-crum-insurance
• Instagraminstagram.com/frankcrumcorp
• TikToktiktok.com/@frankcrumcorp

Compliance2 records

Revenue estimate

Valuation estimate

Number of profiles

Profiles11 records

Subsidiaries1 record

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about Frank Winston Crum Insurance