Business Details
50+ Years
experience
Your Trusted Insurance Partner in Minnesota
Flagship Insurance Services was founded in 1942 with a commitment to delivering tailored insurance solutions to both businesses and individuals. Built upon a tradition of integrity and industry leadership, we combine thoughtful strategic planning with technology-based solutions to ensure sustained customer satisfaction. Our team of specialists brings decades of experience in health insurance, wellness programs, plan design, and strategic planning, having grown the company by over 20% through organic growth and acquisitions. We serve clients across Minnesota, North Dakota, Wisconsin, Florida, Colorado, Arizona, and Texas, offering a full range of insurance products including employee benefits, business insurance, and personal coverage. Our approach emphasizes personalized service, with professionals who act as consultants to explain insurance options and determine unique client needs.We prioritize cost-effective solutions, offering one-stop shopping for a comprehensive array of products and services. Our dedication to excellence is reflected in our long-standing client relationships and proactive strategies to adapt to industry changes. We provide dedicated support from policy selection through claims processing, ensuring clients receive the best combination of price, coverage, and service. With a focus on risk management, we help clients reduce insurance costs through elimination, reduction, transfer, or assumption of risks. Our ongoing reviews of insurance programs ensure continued adequacy and value for clients.
Services
Health Insurance
Auto Insurance
Home Insurance
Business Insurance
Life Insurance
Disability Insurance
Travel Insurance
Employee Benefits
Retirement Plans
Medicare Plans
Details
- Year established: 1942
Highlights and features
- We work for you, not an insurance company, prioritizing your needs.
- Certified professionals with decades of industry expertise and leadership.
- Access to over 40 insurance carriers for competitive pricing and options.
- Founded in 1942, combining tradition with modern, technology-driven solutions.
- Dedicated support from policy selection through claims processing.
What people say
Friendly and reliable
Exceptional service
Proactive support
Competitive pricing
Tailored coverage
Services
Business Insurance
Flagship Insurance Services offers comprehensive business insurance solutions, including property, liability, workers' compensation, and cyber liability coverage. Our team helps businesses of all sizes mitigate risks through tailored policies that protect against financial losses from unforeseen events. With access to multiple carriers, we ensure competitive pricing and customized protection for industries across seven states.
Health Insurance
We provide individual and group health insurance plans, including fully insured, self-funded, and consumer-driven options. Our experts guide clients through ACA compliance, HSA/HRA accounts, and employer-sponsored programs to ensure affordable, comprehensive coverage. Partnerships with major providers like Blue Cross Blue Shield ensure diverse, competitive options for personal and business needs.
Employee Benefits
Our employee benefits services include retirement plans, disability insurance, wellness programs, and HR compliance support. We assist employers with ACA reporting, COBRA administration, and strategic planning to attract talent while managing costs. Dedicated account teams provide benchmarking, online enrollment, and ongoing education for businesses of all sizes.
Life Insurance
We offer term and permanent life insurance policies to safeguard families' financial futures. Coverage protects estates, mortgages, and business investments, with options tailored to individual needs. Our agents help clients navigate policy types, ensuring appropriate coverage amounts and beneficiaries to meet long-term security goals.
Retirement Planning
Flagship provides retirement planning services for individuals and businesses, including 401(k), IRA, and annuity options. We help clients structure tax-advantaged savings plans, rollovers, and investment strategies to achieve financial independence. Personalized guidance ensures alignment with both short-term needs and long-term wealth-building objectives.
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 Flagship by 20% through client-focused solutions and acquisitions.
Nick Kuchenbecker
Chief Growth Officer
Nick earned a B.S. in Business Management from Minnesota State University, Mankato. He has helped over 4,000 clients save $50 million in tax savings through expertise in FSA, HSA, and ACA compliance plans.
Dave Sherman
Founder/Agent
Dave holds a BA in economics/accounting from the University of Minnesota, an MBA from the University of St. Thomas, and a PhD from Pacific Coast University. He has served as CFO for manufacturing companies and leads business insurance and investment strategies.
Erik Westrum
VP of Sales
Erik brings over a decade of insurance sales experience and former professional hockey leadership. He focuses on client relationships, team development, and creating efficient systems to enhance client service and team productivity.
Lisa Brown
Director of Operations
Lisa earned a B.S. in Business Administration and an MBA from Rasmussen University. She manages benefit enrollment services and HR consulting, combining hands-on expertise with technology-driven solutions for Medicare and employee benefits clients.
Questions
What types of insurance does Flagship Insurance Services offer?
We provide health, auto, home, life, disability, travel, business, and retirement insurance, along with employee benefits and Medicare plans for individuals and businesses.
Do you serve clients outside Minnesota?
Yes, we serve clients in North Dakota, Wisconsin, Florida, Colorado, Arizona, and Texas, in addition to Minnesota.
What sets Flagship Insurance apart from other agencies?
We work independently to find the best coverage for you, not tied to a single insurer. Our team offers personalized service, decades of expertise, and access to over 40 carriers.
Do you offer 24/7 claims support?
While we do not provide 24/7 services, our team responds promptly during business hours to assist with claims and coverage questions.
Can you help with ACA compliance for businesses?
Yes, our experts provide ACA reporting, health savings account administration, and compliance consulting to help employers meet regulatory requirements and avoid penalties.
