About Us

Flagship Insurance Services is built upon a tradition of integrity, industry leadership and excellence. We are committed to delivering tailored insurance solutions to both businesses and individuals with thoughtful strategic planning, valuable professional services and technology-based solutions that result in sustained customer satisfaction.

About Us

Flagship Insurance Services is built upon a tradition of integrity, industry leadership and excellence. We are committed to delivering tailored insurance solutions to both businesses and individuals with thoughtful strategic planning, valuable professional services and technology-based solutions that result in sustained customer satisfaction.

About Us

Flagship Insurance Services is built upon a tradition of integrity, industry leadership and excellence. We are committed to delivering tailored insurance solutions to both businesses and individuals with thoughtful strategic planning, valuable professional services and technology-based solutions that result in sustained customer satisfaction.

Founded in 1942

Flagship Insurance Services has a strong reputation for excellence in the products and services we offer. We have grown to provide a full range of insurance solutions for individuals and businesses throughout MN, ND, WI, IA, FL, CO and AZ.

Definition of FLAGSHIP

noun
  1. a ship carrying the commander of a fleet, squadron, or the like, and flies the officer’s flag.
  2. the finest, or most important one of a group of things or system.

Founded in 1942

Flagship Insurance Services has a strong reputation for excellence in the products and services we offer. We have grown to provide a full range of insurance solutions for individuals and businesses throughout MN, ND, WI, IA, FL, CO and AZ.

Definition of FLAGSHIP

noun
  1. a ship carrying the commander of a fleet, squadron, or the like, and flies the officer’s flag.
  2. the finest, or most important one of a group of things or system.

Founded in 1942

Flagship Insurance Services has a strong reputation for excellence in the products and services we offer. We have grown to provide a full range of insurance solutions for individuals and businesses throughout MN, ND, WI, IA, FL, CO and AZ.

Definition of FLAGSHIP

noun
  1. a ship carrying the commander of a fleet, squadron, or the like, and flies the officer’s flag.
  2. the finest, or most important one of a group of things or system.

Meet Our Staff

The Flagship Insurance Services team is made up of specialists dedicated to using their experience and expertise to meet your objectives, and is committed to anticipating and fulfilling your needs. As highly specialized consultants, we have built our reputation for excellence.

Meet Our Staff

The Flagship Insurance Services team is made up of specialists dedicated to using their experience and expertise to meet your objectives, and is committed to anticipating and fulfilling your needs. As highly specialized consultants, we have built our reputation for excellence.

Meet Our Staff

The Flagship Insurance Services team is made up of specialists dedicated to using their experience and expertise to meet your objectives, and is committed to anticipating and fulfilling your needs. As highly specialized consultants, we have built our reputation for excellence.

Jennifer Sherman Stratton

Chief Executive Officer – Owner/CEO

Learn More about Jennifer
Jennifer earned her B.S. in Business from the University of Minnesota, Carlson School of Management. She began her insurance career with Flagship Insurance Services in 1998. Jennifer was selected as a 2012 Five Star Business Insurance and Benefits Professional and serves as Vice Chair on the MN Republican Health Care Reform Task Force. She purchased Flagship Insurance Services in 2012.
Jennifer assists and advises businesses in the management of their employee benefits and assists employees transitioning from an employer plan into Medicare. She takes particular interest in properly vetting employers with 50-200 employees to consider self-insuring and gives mid-size employers the personal attention they need to make a self-insured plan successful. After policies have been established, she offers continued assistance in the capacity of account servicing and acts on the client’s behalf with insurance providers.

Nick Kuchenbecker

Owner

Learn More about Nick
Nick earned his B.S. in Business Management from Minnesota State University, Mankato, and graduated Cum Laude.  Nick has helped over 4000 clients save over 50 million dollars in tax savings over his career.  Nick is an expert when it comes to FSA, HSA, HRA, FHRA, COBRA, QSEHRA, Retiree Billing, FMLA, ERISA, HIPAA, PCORI, ACA, and other related tax and compliance plans relative to employee benefits.

Dave Sherman

Founder/Agent

Learn More about Dave
Dave has 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 holds the designations of CMA (Certified Management Accountant), CPIA (Certified Professional Insurance Agent), and CIC (Certified Insurance Counselor). He specializes in business insurance, employee benefits and investments. David served as CFO (Chief Financial Officer) in two manufacturing companies for a total of 21 years before purchasing the Agency in 1988. Dave is a certified Notary Public.

Curt Stratton

Agent

Learn More about Curt
After graduating from UW-Stout with a B.S in Applied Mathematics, Curt spent the first 26 years of his career in Information Technology as a software developer and people leader. He joined Flagship at the end of 2021 and is applying his analytical skills and attention to detail to help businesses find the right commercial coverage.  Away from the office, Curt enjoys hunting, fishing, cooking, and a good bourbon.

Brooke Kuchenbecker

Agent

Learn More about Brooke
Brooke is a licensed Life and Health Insurance Agent who specializes in Medicare product sales.  Her expertise is in helping seniors and retirees navigate the Medicare health and drug plan marketplace.  She enjoys assisting her clients to find insurance coverage that is cost-effective and tailored to their health needs.  Brooke graduated with a Business Administration/Marketing degree from Minnesota State University Mankato and started her career in the Advertising industry.  Her hobbies include watching her three boys play sports, attending country music concerts, and going on walks.  

Erin Kutz

Agent

Learn More about Erin
Erin graduated from Minnesota State University, Mankato, with a B.S. in Business Management. Prior to joining Flagship Insurance Services in 2006, Erin gained more than 2 years experience with an agency in St. Cloud, MN. Her unique position allows her to sell, service and negotiate all aspects of commercial accounts. Erin is a licensed agent and has earned both CISR (Certified Insurance Service Representative) and CIC (Certified Insurance Counselor) designations.

Katelynn Lahaye

Agent

Learn More about Katelynn
Katelynn Graduated from Iowa State university with a B.S. in Finance and Marketing, and a minor in French. She began working in the insurance industry at a third-party administrator, learning the self-funded side of benefits. She joined the Flagship team in September of 2022 and will be using her expertise to help clients enrich their benefits and find their right solution. Katelynn is an avid traveler and is always looking for a recommendation for future destinations.

Sarah Fasching

Agent

Learn More about Sarah
Sarah earned a Bachelor of Science in Business and Communications from Bemidji State University. She joined Flagship Insurance Services in 2009 and is responsible for the sales and service of personal lines accounts including home, auto and farm insurance. She is a licensed agent and has earned her CISR (Certified Insurance Service Representative) designation.
Sarah is a certified Notary Public.

Dean Hanson

Agent

Learn More about Dean
After attending American Institute of Business in Des Moines Iowa for Business Administration and Financial Management, Dean worked in the Financial Services and Insurance industries for over 25 years.  Dean has worked for companies like American Express Financial Services, Medica Health Plans and TASC.  He has experience selling Long Term Care, Individual, Medicare, Ancillary and Small Group Health Insurance.  Dean joined Flagship in February 2022 and will focus on the small group market in Minnesota and Iowa.  In his spare time Dean enjoys going for walks, dinner with his wife Roxanne, and spending time on his family farm in Northeast Iowa.

Scott Benjamin

Agent

Learn More about Scott
Scott graduated from the University of Minnesota with a B.S. in Agriculture. He completed and passed 5 courses in the Certified Insurance Counselor program. He earned a certificate in Health Care Reform Studies from the American College in Bryn Mawr. He has taken at least 12 other insurance courses, but his favorite course was “How to save Premiums in the Design of Employee Benefit Plans”. This course was taught by an actuary and showed simplified actuarial techniques. He uses these methods every day with his clients and the information gives big dividends. The methods are practical and easy to implement.
Scott works with clients of all sizes and particularly enjoys clients in the 25 to 300 size that are looking at methods to lower costs. Scott advises his clients on methods such as HRA, HSA, and self-insurance. He makes sure that the risk is low or “next to none” and then maximizes the gains. He is very involved in service and renewal activities. And he will help his clients plan far in advance. This makes budgeting and enrollment a much easier process.

Patti Habisch

Account Manager

Learn More about Patti
Patti has spent her entire professional career as a customer service specialist, many of those years in the insurance industry and has earned her CISR (Certified Insurance Service Representative) designation. She joined Flagship Insurance Services in 2013 as a licensed agent to provide customer service support for commercial lines, personal lines, life and health products.

Cindy Engle

Customer Service Representative

Learn More about Cindy
Cindy joined Flagship Insurance Services in 2014 to provide customer service support for our employee benefit clients. She manages our online enrollment as well as onboarding/offboarding services for employers. Cindy takes a hands on approach to servicing that our clients have come to expect. Prior to joining Flagship, Cindy spent 30 years in customer service, servicing individuals in both the legal and medical fields. Cindy is a certified Notary Public.

Leigha Bruns

Account Manager

Learn More about Leigha
Leigha earned her Bachelor of Science degree in Business Administration at Loras College in Dubuque, Iowa. Having worked 2-3 jobs while going to school full-time at Loras, and being actively involved on campus as a peer assistant, CORE team member, and student tours volunteer, Leigha has developed a strong work ethic and maintains her commitment to community and volunteer activities in her free time. She also enjoys painting and traveling, and has a minor in International Studies.
Leigha joined Flagship in 2017 to manage our employee benefits enrollment and administration platforms, tools and resources that give employers a secure online presence to streamline and automate administration, employee engagement and benefits management. She also offers customer service support to our employer groups.

Alyssa Kuck

Customer Service Representative

Learn More about Alyssa
Alyssa joined Flagship Insurance Services in 2019 as a customer service support to assist small and large groups with their employee benefits. She also assists the brokers in creating documentation along with answering any client inquiries throughout the year. Joining the Flagship team with twelve years of experience in customer service and a strong commitment to her work, allows her to provide the best support to our clients.
Aside from work, Alyssa resides in Winsted with her husband Jordan and two sons. She loves to spend time outside, going on walks to the park with her boys, and taking family day trips. She also loves to be involved and attend community events with her family.

Angie Knapp

Customer Service Representative

Learn More about Angie
Angie graduated from Viterbo University in La Crosse, Wisconsin with a Bachelor of Arts degree in 2001.  She spent several years as a customer service representative in the Commercial and Medicare lines.  She joined Flagship in 2022 as a Personal Lines customer service representative and is excited to help individuals with their insurance needs.  She is based in the Winsted office.  During her free time, she enjoys spending time with her family, dog and two cats, listening to music and quilting.

Heather Henning

Customer Service Representative

Learn More about Heather
Check back soon.

Noel Painschab

Receptionist/Office Clerk

Learn More about Noel
Noel began working at the Winsted Flagship office in 2017 as an Office Clerk and Receptionist.  She brought with her 22 years of Customer Service and Office Management experience.  Noel enjoys the ever changing fast pace of being the front receptionist, greeting and helping customers as well as assisting all office personnel throughout the day.
Outside of work, Noel enjoys spending time on her beautiful farm with her husband and her two boys.

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Get In Touch

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© Flagship Insurance Services. All Rights Reserved
Toll-Free 800-786-7208 | Fax 320-485-2199
  • Health Insurance
  • Life & Disability Insurance
  • Home Owners Insurance
  • Auto Insurance
  • Employee Benefits
  • Business Insurance
  • Travel Insurance
  • Personal Umbrella Insurance
  • Renters Insurance
  • Motorcycle Insurance
  • Snowmobile Insurance
  • Boat Insurance
  • RV Insurance
  • Rental or Vacant Properties
  • Workers Compensation
  • General Liability
  • Commercial Auto Insurance
  • Retirement & Investments

© Flagship Insurance Services. All Rights Reserved
Toll-Free 800-786-7208 | Fax 320-485-2199

  • Health Insurance
  • Life & Disability Insurance
  • Home Owners Insurance
  • Auto Insurance
  • Employee Benefits
  • Business Insurance
  • Travel Insurance
  • Personal Umbrella Insurance
  • Renters Insurance
  • Motorcycle Insurance
  • Snowmobile Insurance
  • Boat Insurance
  • RV Insurance
  • Rental or Vacant Properties
  • Workers Compensation
  • General Liability
  • Commercial Auto Insurance
  • Retirement & Investments

© Flagship Insurance Services. All Rights Reserved
Toll-Free 800-786-7208 | Fax 320-485-2199