Cross Insurance

What Cross Insurance does

Cross Insurance, a subsidiary of the family-owned holding company Cross Financial Corp., is one of New England's largest independent insurance intermediaries. Founded in 1954 at the kitchen table of Woodrow Cross in Bangor, Maine, the company has grown over three generations into a multi-line agency operating 40+ branches across the Northeast and Florida with a workforce of more than 1,200 employees. It represents over 100 insurance carriers, distributing personal, commercial, and specialty coverage to individuals, businesses, employers, and institutions.

The company operates four core divisions: Personal Insurance (auto, home, renters, boat, motorcycle, ATV, RV, snowmobile, life, umbrella, including the Cross Private Client Insurance high-value home brand); Commercial Insurance (property, auto/trucking, general liability, umbrella, cyber, professional liability/E&O, EPLI, workers' compensation, inland marine); Employee Benefits (medical, dental, vision, disability, FSA/HSA/HRA/commuter programs via the Cross Benefits Portal, and the exclusive Cross Health Insurance Pod for groups exceeding 200 employees); and Specialty Products (Third Party Administration for self-insured workers' comp trusts, Student Health for higher education, Surety & Bonding licensed in all 50 states, Healthcare professional liability, Construction, and Clean Energy risk solutions). Proprietary technology consists of administrative portals and enrollment/waiver systems rather than AI-driven platforms.

Revenue is generated primarily through carrier commissions on placed business, supplemented by professional-services and managed-services fees from benefits administration and TPA activities, and transaction fees from surety bond issuance. The go-to-market is sales-led through 40+ local branches, augmented by online quote-request channels and channel-partner distribution across its 100+ carrier relationships. The company pursues an aggressive acquisition strategy, having absorbed more than 150 operations since founding, with notable 2022 acquisitions of Patriot Benefit Solutions, Northern Benefits of Massachusetts, Loiselle Insurance Agency, and Maine Insurance Agency of Greater Portland. It has been ranked the 2nd Largest Insurance Broker in Massachusetts by the Boston Business Journal for four consecutive years (2022–2025) and placed in the Top 20 Property & Casualty Agencies by Insurance Journal in 2025.

Name

Cross Insurance

Legal name

Cross Financial Corp.

Website

https://crossagency.com

Company type

Private

Founded year

1954

Operating status

Operating

Headcount range

501–1,000 employees

Short description

Cross Insurance is a third-generation, family-owned independent insurance agency founded in 1954, operating 40+ branches across the Northeast and Florida with 1,200+ employees. It distributes personal, commercial, employee benefits, and specialty insurance products on behalf of 100+ carriers to individuals, businesses, and institutions.

Ownership category

akta.pro rank

Product category

Insurance Brokerage Services

NAICS

Agencies, Brokerages, and Other Insurance Related Activities (5242), Insurance Agencies and Brokerages (52421), Pharmacy Benefit Management and Other Third Party Administration of Insurance and Pension Funds (524292)

SIC

Insurance Agents, Brokers & Service (6411), Surety Insurance (6351)

akta.pro primary industry

Commercial Lines Insurance Brokerage (FSAEADAB)

Keywords

• Independent insurance brokerage
• Commercial insurance coverage
• Employee benefits administration
• Personal lines insurance
• Surety bond services

Headquarters

HQ city

Bangor

HQ country

United States

HQ region

North America

Offices41 records

Markets served

GTM type

B2B and B2C

Offering type

Services

Cost components

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

Revenue model

1. Insurance Commissions: Earn commissions from insurance carriers for placing business. As an independent insurance broker, they represent multiple insurance providers and earn commissions based on policies sold.
2. Employee Benefits Administration: Provides group benefits administration services including medical, dental, vision, and disability plans for businesses, earning fees for plan management and administration.
3. Third Party Administration: TPA services for self-insured workers' compensation trusts, including claims management, loss control, and administrative services.
4. Surety Bond Services: Issuance of various surety bonds including bid bonds, performance bonds, and license bonds, earning fees for bond issuance.
5. Student Health Insurance Plans: Administration of student health plans for colleges and universities, providing implementation, enrollment, and ongoing account management.

Pricing tiers

Go-to-market motion2 records

Distribution channels4 records

Marketing channels5 records

Core offering

Cross Insurance is an independent insurance brokerage that distributes personal lines, commercial lines, employee benefits, and specialty insurance products (including surety bonds, student health plans, and third-party workers' compensation administration) on behalf of over 100 insurance carriers. The firm operates through a network of 40+ branch offices across the Northeast and Florida, pairing local agent service with multi-carrier comparison and quote-based placement. Revenue is generated primarily through carrier commissions, benefits administration fees, and TPA service fees.

Product overview

Cross Insurance is a third-generation family-owned insurance agency founded in 1954, operating as one of New England's largest independent insurance intermediaries. The company offers a comprehensive insurance portfolio organized into four core divisions: Personal Insurance (auto, home, renters, boat, motorcycle, ATV, RV, snowmobile, life, and umbrella), Commercial Insurance (property, auto, general liability, umbrella liability, cyber, professional liability, EPLI, workers' comp, and inland marine), Employee Benefits (medical, dental, vision, disability with the Cross Health Insurance Pod and Cross Benefits Portal), and Specialty Products (Third Party Administration, Student Health, Surety & Bonding, Higher Education, Healthcare, Construction, and Clean Energy). Cross Insurance represents over 100 insurance carriers and maintains over 40 office locations throughout the Northeast and Florida.

Differentiator

Problem solved

Functional benefit

Products and services

• Personal Insurance Personal lines insurance brokerage covering auto, home, renters, boat, motorcycle, ATV, RV, snowmobile, life, and umbrella for individuals and families, placed across more than 100 carriers with local agent service at 40+ branch offices.
• Auto Insurance Vehicle insurance covering cars, motorcycles, antique autos, ATVs, snowmobiles, and RVs with options for liability, collision, comprehensive, gap, and towing coverage; priced on vehicle type, driving history, location, and coverage selections with multi-policy, multi-car, low-mileage, hybrid/electric, good student, and pay-in-full discounts.
• Home Insurance Homeowners insurance covering fire, theft, water damage, and plumbing issues with options for high-value, historic, coastal, and second homes, including specialized coverage through Cross Private Client Insurance; priced on home size, location, coverage limits, and claims history.
• Renters Insurance Insurance for rented properties covering personal property replacement and liability protection for tenants.
• Boat Insurance Watercraft insurance covering powerboats, fishing boats, sailboats, pontoon boats, and personal watercraft including collision, theft, fire, and accessory coverage.
• Motorcycle Insurance Motorcycle coverage including full replacement, accessories, comprehensive, and possessions coverage for riders.
• Umbrella Insurance Additional personal liability protection extending beyond home or auto policy limits for property damage, lawsuits, injuries, and personal liability situations.
• Commercial Insurance Business insurance brokerage covering commercial property, commercial auto and trucking, general liability, umbrella liability, cyber, professional liability, EPLI, workers' compensation, and inland marine for small to large businesses.
• Commercial Property Insurance Coverage for business furniture, inventory, equipment, buildings, outdoor signage, and landscaping against vandalism, wind, hail, and fire.
• Commercial Auto & Trucking Insurance Vehicle insurance for businesses covering medical expenses, property damage, collision, hired auto, non-owned auto, and uninsured motorist coverage.
• General Liability Insurance Coverage for bodily injury, property damage, copyright infringement, and product liability claims against businesses.
• Cyber Insurance Coverage for legal fees, customer notification of data breaches, compromised data recovery, and computer system repairs following cyber attacks.
• Professional Liability Insurance Errors and Omissions coverage protecting against claims from clients for mistakes causing financial loss, including clerical errors, misunderstandings, missed deadlines, and inaccurate advice.
• Employment Practices Liability Insurance (EPLI) Coverage protecting against employee claims including harassment, discrimination, wrongful termination, retaliation, and wrongful failure to promote.
• Workers' Compensation Insurance Coverage for workplace injuries and illness including medical bills, a portion of lost wages, and ongoing care costs for employees.
• Inland Marine Insurance Coverage for business property transported over land or temporarily stored offsite, including equipment, products, parts, materials, and high-value items.
• Employee Benefits Group benefits brokerage offering medical, dental, vision, short/long-term disability, life, and worksite benefits for businesses across the Northeast, delivered by over 140 Employee Benefits professionals.
• Student Health / College Health Student health plan administration for colleges and universities in New England, providing comprehensive health, accident, and sports coverage with dedicated account management, online enrollment, and waiver systems. Customers include Bates College, Colby College, Husson University, Maine Maritime Academy, and Worcester Polytechnic Institute.
• Third Party Administration (TPA) Self-insured workers' compensation trust management in Maine through Cross Insurance TPA, Inc., offering competitive pricing, potential premium refunds, and 24/7 claims management access for trusts in manufacturing, construction, forestry, social services, and education sectors.
• Surety & Bonding Full-service surety bond agency handling bid bonds, performance and payment bonds, warranty bonds, subdivision bonds, license and permit bonds, court bonds, commercial surety, and fidelity bonds; licensed in all 50 states.
• Construction Insurance Insurance for contractors and construction companies covering general liability, workers' comp, business assets, surety bonds, business auto, and builder's risk for general contractors, electricians, HVAC, landscapers, masons, painters, plumbers, roofers, and subcontractors.
• Healthcare Insurance Medical professional liability coverage for hospitals, physicians, and aging service facilities in Northern New England, including captives and group trusts for alternative risk programs, as well as reinsurance, workers' comp, property, D&O/EPLI, and regulatory coverage.
• Higher Education Insurance Insurance solutions for colleges and universities including Owner Controlled Insurance Programs (OCIPs), wrap-ups, and the Educational Sustainability Risk Practice for renewable energy coverage through multi-national insurers and Lloyd's of London.
• Clean Energy Insurance Risk and insurance solutions for renewable energy assets including wind, solar, bioenergy, small-hydro, geothermal, wave and tidal, and carbon capture sectors, covering development, construction, and operation phases.
• Cross Private Client Insurance High-value home insurance brand serving clients with historic homes, coastal homes, and second homes requiring specialized coverage beyond typical homeowners policies.

Quantifiable outcome

• 2nd Largest Insurance Broker in Massachusetts (2022, 2023, 2024, 2025)
• +2 more outcomes

Named customers12 records

Segments8 records

Ideal customer profiles7 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Feature3 records

Partnerships

15 partnerships are on record, tiered core.

• Gillette StadiumcoreGTM or Marketing PartnerOfficial insurance broker for Gillette Stadium, providing insurance services and visibility through stadium sponsorship and branding opportunities.
• Boston BruinscoreGTM or Marketing PartnerOfficial insurance broker for the Boston Bruins NHL team, with branding and sponsorship integration.
• Boston Red SoxcoreGTM or Marketing PartnerOfficial insurance broker for the Boston Red Sox MLB team, providing insurance services and marketing visibility.
• New England PatriotscoreGTM or Marketing PartnerOfficial insurance broker for the New England Patriots NFL team with comprehensive sponsorship arrangement.
• New England RevolutioncoreGTM or Marketing PartnerOfficial insurance broker for the New England Revolution MLS soccer team.
• Portland Sea DogscoreGTM or Marketing PartnerOfficial insurance broker for the Portland Sea Dogs minor league baseball team.
• New England Patriots FoundationcoreGTM or Marketing PartnerCornerstone Partner of the New England Patriots Foundation, supporting their mission to aid individuals and families often marginalized.
• Construction Services Group TrustcoreStrategic or Co-development PartnerSelf-insured workers' compensation trust for construction industry employers in Maine, administered by Cross Insurance TPA, Inc.
• Distributors & Suppliers Group TrustcoreStrategic or Co-development PartnerSelf-insured workers' compensation trust for distributors and suppliers in Maine, administered by Cross Insurance TPA, Inc.
• Forest Products Group TrustcoreStrategic or Co-development PartnerSelf-insured workers' compensation trust for forestry and forest products industry in Maine, administered by Cross Insurance TPA, Inc.
• Maine State Group TrustcoreStrategic or Co-development PartnerComprehensive self-insured workers' compensation trust serving various industries in Maine, administered by Cross Insurance TPA, Inc.
• Manufacturers of Maine Group TrustcoreStrategic or Co-development PartnerSelf-insured workers' compensation trust for manufacturing companies in Maine, administered by Cross Insurance TPA, Inc.
• Maine Oil Dealers' Association Workers Compensation Insurance TrustcoreStrategic or Co-development PartnerIndustry-specific self-insured workers' compensation trust for energy marketers in Maine, administered by Cross Insurance TPA, Inc.
• Social Services & Education Group TrustcoreStrategic or Co-development PartnerSelf-insured workers' compensation trust for social services and education organizations in Maine, administered by Cross Insurance TPA, Inc.
• Greater Portland FivecoreStrategic or Co-development PartnerSelf-insured workers' compensation trust group for employers in the Greater Portland, Maine area, administered by Cross Insurance TPA, Inc.

Scale indicators8 records

Recent moves7 records

Expansion highlights6 records

Direct peers

• USI Insurance Services: Large US middle-market insurance brokerage with an aggressive Northeast and national acquisition roll-up strategy and significant employee benefits practice. Closely comparable to Cross in target customer mix (mid-market commercial, personal lines, benefits) and acquisition-driven growth model, though materially larger and PE-backed (KKR).
• Hub International: North American insurance brokerage that grew from a regional platform into a national player via aggressive acquisition of independent agencies, with deep employee benefits and commercial lines capabilities. Highly comparable to Cross in M&A-led expansion, multi-carrier independence, and benefits-brokerage emphasis.
• Brown & Brown: Publicly traded US insurance brokerage built largely through regional acquisitions of independent agencies, with strong programs, employee benefits, and personal lines divisions. Comparable to Cross as a diversified, multi-region independent broker pursuing organic and inorganic growth.
• The Hilb Group: Mid-Atlantic and Northeast-focused insurance brokerage founded by a former Hub executive, pursuing a regional acquisition roll-up of personal, commercial, and benefits agencies. A direct comparability fit for Cross's geography, M&A model, and product mix.
• World Insurance Associates: PE-backed US insurance brokerage executing a rapid Northeast-anchored roll-up of independent agencies, with strong personal and commercial lines growth. Closely mirrors Cross's branch expansion and acquisition cadence across the Northeast corridor.
• Insurance Office of America: Privately held, family-founded US insurance brokerage with a multi-state footprint built through acquisitions and a diversified personal, commercial, employee benefits, and surety offering. Comparable to Cross in family ownership, product breadth, and acquisition-led regional expansion.
• Trucordia (formerly PCF Insurance Services): PE-backed US insurance brokerage built via roll-up of independent agencies with personal, commercial, and benefits practices nationwide. Comparable to Cross in acquisition-led model, agency-style distribution, and product breadth, though at larger scale and broader geography.

Emerging players

• Acrisure: Fast-growing, technology-forward insurance brokerage built through hundreds of agency acquisitions, combining personal, commercial, and benefits distribution with proprietary technology investments. Comparable to Cross in M&A intensity and multi-line offering, but with materially more tech differentiation and capital.

Broad incumbents

• Arthur J. Gallagher & Co. One of the largest publicly traded global insurance brokerages and risk management consultancies, with deep commercial, benefits, and specialty capabilities. Comparable to Cross across most product lines but operates at vastly greater scale and as a broad incumbent rather than a regional specialist.
• Marsh McLennan Agency: Middle-market brokerage arm of global insurance broker Marsh McLennan, focused on US commercial and employee benefits distribution. Comparable to Cross on commercial and benefits product lines, but operates as a division of a much larger global incumbent with broader risk advisory capabilities.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat5 records

Key risks5 records

Key highlights1 record

Customer concentration

• Facebookfacebook.com/CrossInsurance
• LinkedInlinkedin.com/company/cross-insurance
• Instagraminstagram.com/cross.insurance
• Xx.com/crossagency1

Revenue estimate

Valuation estimate

Number of profiles

Profiles6 records

Subsidiaries4 records

Funding overview

Funding rounds

Investors

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

M&A3 records

Investments

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

Frequently asked questions about Cross Insurance