Flagship Insurance Services

What Flagship Insurance Services does

Flagship Insurance Services, LLC is an independent insurance agency headquartered in Winsted, Minnesota, founded in 1942 and operating as a privately held, owner-operated LLC. The firm distributes personal and commercial insurance products on behalf of 25+ preferred carriers—including Blue Cross and Blue Shield of Minnesota, Medica, Mutual of Omaha, Aetna, MetLife, The Hartford, Travelers, and Progressive—and is licensed across seven U.S. states (MN, ND, WI, FL, CO, AZ, TX), with four physical offices in Minnesota (Winsted, Shakopee, St. Louis Park, St. Cloud). The product portfolio spans personal lines (home, auto, life, health, disability, Medicare, travel, umbrella, specialty vehicles) and commercial lines (workers compensation, general liability, commercial auto, umbrella, employee benefits), with no proprietary underwriting platform; core technology is a mix of carrier-supplied rating systems, the third-party EZLynx customer service portal, and Zywave's HR360 content platform that supports bundled HR consulting and an attorney hotline for employer clients.

The agency operates on a consultative, sales-led go-to-market, with licensed agents acting as advisors who quote across multiple carriers to identify the best price-coverage-service combination for each client. Revenue is generated primarily through carrier commissions on placed policies, supplemented by fees tied to HR consulting and benefits enrollment services. The customer base is horizontally diversified across individuals, families, small and mid-sized businesses, and Medicare-eligible seniors, with named enterprise relationships including a school district, a manufacturing/technology firm, and a survey/ballot systems company. The business is led by CEO and Owner Jennifer Sherman Stratton (who has grown the firm more than 20% over the past decade through organic growth and acquisition) and President Erik Westrum, with founder Dave Sherman—purchaser of the agency in 1988—continuing in an agent capacity. Day-to-day operations are supported by a roster of licensed producers holding CIC, CPIA, and CISR designations across personal lines, commercial lines, employee benefits, and Medicare verticals.

Name

Flagship Insurance Services

Legal name

Flagship Insurance Services, LLC

Website

https://flagshipinsuranceservices.com

Company type

Private

Founded year

1942

Operating status

Operating

Headcount range

11–50 employees

Short description

Flagship Insurance Services is an independent, owner-operated insurance agency founded in 1942, distributing personal and commercial policies from 25+ carriers across seven U.S. states to individuals, families, employers, and Medicare-eligible seniors.

Ownership category

akta.pro rank

Headquarters

HQ city

Winsted

HQ country

United States

HQ region

North America

Offices4 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: As an independent insurance agency, Flagship Insurance Services earns commissions from insurance carriers for policies placed on behalf of clients. They represent multiple preferred insurance partners and offer one-stop shopping across a full range of insurance products and services.

Go-to-market motion1 record

Distribution channels2 records

Marketing channels3 records

Core offering

Flagship Insurance Services is an independent insurance agency that sells and services personal lines (auto, home, life, health, disability, Medicare, travel, umbrella, specialty vehicles), commercial lines (workers compensation, general liability, commercial auto, umbrella), and employee benefits (group health, retirement, HR consulting) on behalf of 25+ carrier partners. The agency places policies with multiple insurers, advises clients on coverage selection, and provides claims support, bundling individual and business insurance through licensed agents across Minnesota, North Dakota, Wisconsin, Florida, Colorado, Arizona, and Texas.

Product overview

Flagship Insurance Services is an independent insurance agency founded in 1942, offering a broad portfolio of insurance products and HR services to both individuals and businesses. The core offering consists of personal insurance products (homeowners, renters, auto, life, health, disability, Medicare, travel, and umbrella coverage) and commercial/business insurance products (employee benefits, workers compensation, general liability, commercial auto, and umbrella insurance). Supporting the commercial insurance offerings is an HR services platform featuring the HR Library (compliance tools, employee handbook builders, job description and salary benchmarking tools), Attorney Hotline (HR legal consultation), and HRNOW/HR consulting services for benefits enrollment and administration. The company operates as an independent agency representing multiple insurance carriers including Blue Cross and Blue Shield of Minnesota, Medica, Mutual of Omaha, Aetna, MetLife, and others. The product architecture is not a unified SaaS platform but rather a collection of insurance products supported by digital tools and third-party platforms (EZLynx for client portal, HR360/Zywave for HR content) that facilitate quote, enrollment, and policy management workflows.

Differentiator

Problem solved

Functional benefit

Products and services

• Employee Benefit Programs Comprehensive employee benefits solutions for employers, including group health insurance, wellness programs, plan design, and benefits enrollment administered through HRNOW and HR consulting platforms.
• Business Insurance
• Health Insurance
• Life Insurance
• Disability Insurance
• Auto Insurance
• Home Owners Insurance
• Travel Insurance
• Retirement & Investments
• Workers Compensation
• General Liability
• Umbrella Insurance
• Renters Insurance
• Specialty Vehicle Insurance (Motorcycle, Snowmobile, Boat, RV)
• Medicare Plans
• HR Connection Services (HR360 Library, Attorney Hotline, HRNOW)

Quantifiable outcome

• Over 20% growth over the past decade through organic growth and acquisition

Named customers3 records

Segments3 records

Ideal customer profiles3 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Partnerships

25 partnerships are on record, tiered core and minor.

• Blue Cross and Blue Shield of MinnesotacoreChannel Partner/ Reseller/ DistributorFlagship Insurance Services is an authorized independent agency for Blue Cross and Blue Shield of Minnesota. They sell and service Blue Cross and Blue Shield products to individual and group clients in Minnesota.
• MedicaminorChannel Partner/ Reseller/ DistributorPreferred insurance partner listed on the company's partner logo wall. Medica is a health insurance carrier.
• Mutual of OmahaminorChannel Partner/ Reseller/ DistributorPreferred insurance partner listed on the company's partner logo wall. Mutual of Omaha provides health, life, and Medicare insurance products.
• AetnaminorChannel Partner/ Reseller/ DistributorPreferred insurance partner listed on the company's partner logo wall. Aetna provides health and related insurance products.
• MetlifeminorChannel Partner/ Reseller/ DistributorPreferred insurance partner listed on the company's partner logo wall. Metlife provides life, dental, and other insurance products.
• The HartfordminorChannel Partner/ Reseller/ DistributorPreferred insurance partner listed on the company's partner logo wall. The Hartford provides business and personal insurance products.
• TravelersminorChannel Partner/ Reseller/ DistributorPreferred insurance partner listed on the company's partner logo wall. Travelers provides property and casualty insurance products.
• ProgressiveminorChannel Partner/ Reseller/ DistributorPreferred insurance partner listed on the company's partner logo wall. Progressive provides auto and personal insurance.
• Hanover Insurance GroupminorChannel Partner/ Reseller/ DistributorPreferred insurance partner listed on the company's partner logo wall. Hanover provides commercial and personal insurance.
• Lincoln Financial GroupminorChannel Partner/ Reseller/ DistributorPreferred insurance partner listed on the company's partner logo wall. Lincoln Financial Group provides retirement and insurance solutions.
• Foremost Insurance GroupminorChannel Partner/ Reseller/ DistributorPreferred insurance partner listed on the company's partner logo wall. Foremost provides specialty insurance products.
• Sanford Health PlanminorChannel Partner/ Reseller/ DistributorPreferred insurance partner listed on the company's partner logo wall. Sanford Health Plan provides health insurance products.
• Principal Financial GroupminorChannel Partner/ Reseller/ DistributorPreferred insurance partner listed on the company's partner logo wall. Principal provides retirement and insurance solutions.
• GenworthminorChannel Partner/ Reseller/ DistributorPreferred insurance partner listed on the company's partner logo wall. Genworth provides long-term care insurance and mortgage insurance.
• WestbendminorChannel Partner/ Reseller/ DistributorPreferred insurance partner listed on the company's partner logo wall. Westbend provides property and casualty insurance.
• Western National InsuranceminorChannel Partner/ Reseller/ DistributorPreferred insurance partner listed on the company's partner logo wall.
• Delta DentalminorChannel Partner/ Reseller/ DistributorPreferred insurance partner listed on the company's partner logo wall. Delta Dental provides dental insurance products.
• HealthPartnersminorChannel Partner/ Reseller/ DistributorPreferred insurance partner listed on the company's partner logo wall. HealthPartners provides health insurance products.
• ING (Voya Financial)minorChannel Partner/ Reseller/ DistributorPreferred insurance partner listed on the company's partner logo wall. ING/Voya provides retirement and investment products.
• Auto-Owners InsuranceminorChannel Partner/ Reseller/ DistributorPreferred insurance partner listed on the company's partner logo wall. Auto-Owners provides auto, home, and business insurance.
• Grinnell MutualminorChannel Partner/ Reseller/ DistributorPreferred insurance partner listed on the company's partner logo wall. Grinnell Mutual provides property and casualty insurance.
• North Star Resource GroupminorChannel Partner/ Reseller/ DistributorPreferred insurance partner listed on the company's partner logo wall. North Star provides employee benefits and insurance products.
• Preferred OneminorChannel Partner/ Reseller/ DistributorPreferred insurance partner listed on the company's partner logo wall. Preferred One provides health insurance products.
• IMG (International Medical Group)minorChannel Partner/ Reseller/ DistributorPreferred insurance partner listed on the company's partner logo wall. IMG provides international health and travel insurance.
• American Collectors InsuranceminorChannel Partner/ Reseller/ DistributorPreferred insurance partner listed on the company's partner logo wall. American Collectors Insurance specializes in collector vehicle insurance.

Scale indicators2 records

Recent moves6 records

Expansion highlights5 records

Direct peers

• IMA Financial Group: Mid-market independent insurance brokerage focused on commercial, personal, and employee benefits lines with a consultative, multi-carrier distribution approach similar to Flagship's.
• Hilb Group: Middle-market insurance brokerage operating across personal, commercial, and benefits lines via partner agencies in multiple states; comparable in scale and product breadth to Flagship.
• LeClair Insurance Agency: Independent Minnesota-based insurance agency offering personal, commercial, and employee benefits products with a similar consultative, multi-carrier model — directly comparable in geography, product mix, and customer base.
• Cross Insurance: Northeast regional independent insurance agency offering personal, commercial, and benefits products through a multi-carrier model; structurally analogous to Flagship.

Broad incumbents

• Acrisure: Rapidly growing, tech-enabled insurance brokerage with broad commercial and personal lines capabilities; competes in the same independent-agency-acquisition channel that Flagship participates in.
• HUB International: Large North American insurance brokerage with a broad product set including personal, commercial, and benefits — a wider portfolio competitor to Flagship's commercial and benefits practice.
• Brown & Brown: Large publicly traded national insurance brokerage with personal, commercial, and benefits lines; competes with Flagship's commercial book in larger accounts and through acquisitive expansion into its geographies.
• Arthur J. Gallagher & Co. Global insurance brokerage and risk management firm operating across commercial, benefits, and personal lines, including a sizable Midwest regional agency footprint that overlaps with Flagship.
• Marsh McLennan: World's largest insurance broker and risk adviser, with substantial benefits and personal-lines practice; a broad-market incumbent against whom Flagship must position on customer intimacy.

Others

• Keystone Insurers Group: Alliance/network of independent insurance agencies providing carrier access, operational support, and shared resources to member agencies like Flagship — an ecosystem enabler rather than a direct competitor.

Market position

Strengths4 records

Weaknesses4 records

Competitive moat4 records

Key risks5 records

Key highlights6 records

Customer concentration

• Facebookfacebook.com/flagshipinsuranceservices
• Xx.com/FlagshipIns
• LinkedInlinkedin.com/company/flagship-insurance-services-inc

Revenue estimate

Valuation estimate

Number of profiles

Profiles12 records

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 Flagship Insurance Services