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Business Details
50+ Years
experience
Your Trusted Insurance Partner in Minneapolis
Flagship Insurance Services is built upon a tradition of integrity, industry leadership, and excellence. We are committed to delivering tailored insurance solutions with thoughtful strategic planning, valuable professional services, and technology-based solutions that result in sustained customer satisfaction. Founded in 1942, our agency has grown to provide a full range of insurance solutions for individuals and businesses across multiple states. Our team of certified professionals works as your consultant to explain insurance options, determine unique needs, and offer a choice of plans that balance price, coverage, and service.

We prioritize risk management strategies to reduce costs while maintaining comprehensive protection. Our dedication to compliance, ongoing education, and personalized support ensures clients receive accurate advice and efficient claims handling. With partnerships spanning over 40 insurance providers, we deliver one-stop shopping for diverse insurance products, from health and life insurance to commercial auto and cyber liability coverage.
Services
Employee Benefits Business Insurance Healthcare Insurance Life Insurance Auto Insurance Home Insurance Travel Insurance Retirement Plans Disability Insurance Cyber Liability
Details
  • Year established: 1942
Highlights and features
  • We have over 80 years of experience in the insurance industry.
  • Our team offers certified expertise in healthcare reform and compliance.
  • We provide access to over 40 insurance carriers for competitive options.
  • We deliver personalized risk management strategies to reduce costs.
  • Our dedicated account teams ensure ongoing support and policy reviews.
Associations and certifications
  • Blue Cross and Blue Shield of Minnesota
What people say
Personalized service Knowledgeable staff Comprehensive options Dedicated support Competitive rates
Services
Employee Benefits
We design comprehensive employee benefit programs including health, dental, disability, and retirement plans. Our experts help employers navigate compliance with ACA, HIPAA, and ERISA regulations while optimizing costs. Services include carrier negotiation, online enrollment, and strategic planning to attract and retain talent through competitive benefits packages.
Business Insurance
Our business insurance solutions protect companies against property damage, liability claims, and operational risks. Offerings include general liability, workers' compensation, cyber liability, and professional liability coverage. We tailor policies for industries ranging from manufacturing to healthcare, ensuring protection against equipment breakdowns, crime, and directors' liability.
Healthcare Insurance
We provide individual and group healthcare plans through partnerships with major providers like Blue Cross Blue Shield. Services include Medicare, ACA-compliant plans, and consumer-driven health accounts (HSA, FSA). Our team simplifies enrollment, compares premiums, and ensures coverage aligns with clients' medical and financial needs.
Life Insurance
Our life insurance offerings include term and permanent policies to protect families and businesses. We help clients secure financial stability for dependents, cover mortgages, and plan estate strategies. Policies are available for individuals and key employee protection in corporate settings.
Auto Insurance
We offer auto insurance for personal and commercial vehicles, including motorcycles, RVs, boats, and collector cars. Coverage options protect against accidents, theft, and liability claims. Our agents compare rates across providers to ensure competitive pricing for preferred and high-risk drivers.
People
Jennifer Sherman Stratton
Chief Executive Officer
With nearly 30 years in employee benefits, Jennifer specializes in health insurance and strategic planning. She holds dual degrees from the University of Minnesota and has grown the company by 20% through client-focused solutions.
Nick Kuchenbecker
Chief Growth Officer
Nick earned a business degree from Minnesota State University and has helped 4,000+ clients save $50M in tax savings. He specializes in FSA, HSA, and ACA compliance strategies.
Dave Sherman
Founder/Agent
Dave holds economics and MBA degrees with certifications in accounting and insurance. He served as CFO for manufacturing firms before leading the agency since 1988, combining financial expertise with insurance solutions.
Erik Westrum
VP of Sales
A former hockey player and leadership coach, Erik brings 10+ years of insurance sales experience. He focuses on client relationships and team development while balancing family life in Prior Lake.
Lisa Brown
Director of Operations
Lisa earned an MBA from Rasmussen University and manages HRNOW services. She specializes in Medicare and employee benefits, balancing client support with family life and outdoor activities.
Questions
What types of insurance does Flagship Insurance Services offer?
We provide health, life, auto, home, business, disability, travel, and retirement insurance, along with employee benefits and specialized commercial coverage.
How can I get a quote for insurance coverage?
Request a quote online through our website or contact us directly at 800-786-7208 for personalized assistance with our agents.
Do you serve clients outside of Minnesota?
Yes, we serve clients in North Dakota, Wisconsin, Florida, Colorado, Arizona, and Texas in addition to Minnesota.
What sets Flagship Insurance apart from competitors?
We offer access to 40+ carriers, certified expertise in compliance, and personalized risk management strategies tailored to individual and business needs.
Can you help with ACA compliance for businesses?
Yes, our team specializes in Affordable Care Act compliance, including reporting, HSAs, and employer mandate requirements for businesses of all sizes.