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), CIC (Certified Insurance Counselor) and has a Series 6 investment license. 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.
Securities offered through Aegis Investments, Inc., 4915 W 35th St, Suite 206, St Louis Park, MN 55416, 612-336-4432

Cliff Hanson

Agent

Learn More about Cliff
Cliff entered the employee benefits industry in 2002. His specialty is showing our group clients how to think differently when purchasing and utilizing health care insurance by using Health Reimbursement Arrangements (HRAs), Health Savings Accounts (HSAs) and other creative alternatives. Over the years, he has demonstrated how these tools can significantly reduce plan costs for our clients. Cliff is a member of the Plymouth Rotary Club, and the Minnesota Association of Health Underwriters (MAHU).

Tim Marks

Agent

Learn More about Tim
Tim earned his B.S. in Business Administration and Economics from Mankato State University in 1984. He began his insurance career with State Bond and Mortgage Company in New Ulm MN. In 1987, he entered the field of Employee Benefits, where he has focused his practice for the past 30 years.Tim assists his clients with all aspects of their Employee Benefits offerings. He has earned a reputation with the local Health Insurance Companies for his aggressive negotiation skills at renewal time. He also prides himself for being extremely responsive to his clients.

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.

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.

Tom Slater

Agent

Learn More about Tom
Tom joined the Flagship family as a personal lines producer. With an extensive medical background, Tom entered the insurance world by way of employee benefits. He’s spent the last couple years broadening his knowledge by focusing on property and casualty. A Roseville native, Tom now resides in Edina with his wife Amber and children Cole and Charlotte and works primarily out of Flagship’s Edina office.
Tom loves being involved with his kid’s athletics, and being an active member of his church. Whether up at the cabin or acting as that embarrassing parent dancing in the car as he’s dropping his son off at middle school, he loves to have fun and laugh. He’s co-founder of a non-profit, and has led many medical mission trips to Haiti. He believes in helping others, which is why his favorite quote is, “What we do for ourselves dies with us. What we do for others and the world remains and is immortal.” – Albert Pine

Eileen Vasko

Agent

Learn More about Eileen
Eileen began her career in the insurance industry in 1986, providing customer service for an insurance agency in Bloomington, Minnesota. She took a brief hiatus in 1993 to raise a family but returned to the field in 1998. Eileen joined Flagship Insurance Services in 2013 as a licensed agent for sales and service of individual life and health products, including Medicare. Eileen also assists and advises small employers down to 2 employees who want to offer employee benefits. She is certified in the Private Health Insurance Market to find the best health solution for individuals and small employers. Eileen is a certified Notary Public.

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

Customer Service Representative

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

Customer Service Representative

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.

Annie Baide

VP Human Resources

Learn More about Annie
Annie joined Flagship Insurance Services in 2018 and brought a wealth of knowledge & experience to our Agency Management role. Annie graduated from Rasmussen Business College with a degree in Legal Office/Business Office Management in 2004. Since that time, she has worked in the Insurance Industry, with many years in Human Resources, Accounting & Office Management. Annie has a comprehensive knowledge of the insurance industry regarding Personal Lines, Farm, Life, Retirement plans, Health Insurance and Agency Management. Annie has achieved a CIC (Certified Insurance Counselor) designation as well as an Accredited Customer Service Representative designation in Personal Lines.

Jeffrey Jennings

Agent

Learn More about Jeff
Jeff services property and casualty clients around the St. Cloud area.

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.

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), CIC (Certified Insurance Counselor) and has a Series 6 investment license. 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.
Securities offered through Aegis Investments, Inc., 4915 W 35th St, Suite 206, St Louis Park, MN 55416, 612-336-4432

Cliff Hanson

Agent

Learn More about Cliff
Cliff entered the employee benefits industry in 2002. His specialty is showing our group clients how to think differently when purchasing and utilizing health care insurance by using Health Reimbursement Arrangements (HRAs), Health Savings Accounts (HSAs) and other creative alternatives. Over the years, he has demonstrated how these tools can significantly reduce plan costs for our clients. Cliff is a member of the Plymouth Rotary Club, and the Minnesota Association of Health Underwriters (MAHU).

Tim Marks

Agent

Learn More about Tim
Tim earned his B.S. in Business Administration and Economics from Mankato State University in 1984. He began his insurance career with State Bond and Mortgage Company in New Ulm MN. In 1987, he entered the field of Employee Benefits, where he has focused his practice for the past 30 years.Tim assists his clients with all aspects of their Employee Benefits offerings. He has earned a reputation with the local Health Insurance Companies for his aggressive negotiation skills at renewal time. He also prides himself for being extremely responsive to his clients.

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.

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.

Tom Slater

Agent

Learn More about Tom
Tom joined the Flagship family as a personal lines producer. With an extensive medical background, Tom entered the insurance world by way of employee benefits. He’s spent the last couple years broadening his knowledge by focusing on property and casualty. A Roseville native, Tom now resides in Edina with his wife Amber and children Cole and Charlotte and works primarily out of Flagship’s Edina office.
Tom loves being involved with his kid’s athletics, and being an active member of his church. Whether up at the cabin or acting as that embarrassing parent dancing in the car as he’s dropping his son off at middle school, he loves to have fun and laugh. He’s co-founder of a non-profit, and has led many medical mission trips to Haiti. He believes in helping others, which is why his favorite quote is, “What we do for ourselves dies with us. What we do for others and the world remains and is immortal.” – Albert Pine

Eileen Vasko

Agent

Learn More about Eileen
Eileen began her career in the insurance industry in 1986, providing customer service for an insurance agency in Bloomington, Minnesota. She took a brief hiatus in 1993 to raise a family but returned to the field in 1998. Eileen joined Flagship Insurance Services in 2013 as a licensed agent for sales and service of individual life and health products, including Medicare. Eileen also assists and advises small employers down to 2 employees who want to offer employee benefits. She is certified in the Private Health Insurance Market to find the best health solution for individuals and small employers. Eileen is a certified Notary Public.

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

Customer Service Representative

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

Customer Service Representative

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.

Annie Baide

VP Human Resources

Learn More about Annie
Annie joined Flagship Insurance Services in 2018 and brought a wealth of knowledge & experience to our Agency Management role. Annie graduated from Rasmussen Business College with a degree in Legal Office/Business Office Management in 2004. Since that time, she has worked in the Insurance Industry, with many years in Human Resources, Accounting & Office Management. Annie has a comprehensive knowledge of the insurance industry regarding Personal Lines, Farm, Life, Retirement plans, Health Insurance and Agency Management. Annie has achieved a CIC (Certified Insurance Counselor) designation as well as an Accredited Customer Service Representative designation in Personal Lines.

Jeffrey Jennings

Agent

Learn More about Jeff
Jeff services property and casualty clients around the St. Cloud area.

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.

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), CIC (Certified Insurance Counselor) and has a Series 6 investment license. 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.
Securities offered through Aegis Investments, Inc., 4915 W 35th St, Suite 206, St Louis Park, MN 55416, 612-336-4432

Cliff Hanson

Agent

Learn More about Cliff
Cliff entered the employee benefits industry in 2002. His specialty is showing our group clients how to think differently when purchasing and utilizing health care insurance by using Health Reimbursement Arrangements (HRAs), Health Savings Accounts (HSAs) and other creative alternatives. Over the years, he has demonstrated how these tools can significantly reduce plan costs for our clients. Cliff is a member of the Plymouth Rotary Club, and the Minnesota Association of Health Underwriters (MAHU).

Tim Marks

Agent

Learn More about Tim
Tim earned his B.S. in Business Administration and Economics from Mankato State University in 1984. He began his insurance career with State Bond and Mortgage Company in New Ulm MN. In 1987, he entered the field of Employee Benefits, where he has focused his practice for the past 30 years.Tim assists his clients with all aspects of their Employee Benefits offerings. He has earned a reputation with the local Health Insurance Companies for his aggressive negotiation skills at renewal time. He also prides himself for being extremely responsive to his clients.

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.

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.

Tom Slater

Agent

Learn More about Tom
Tom joined the Flagship family as a personal lines producer. With an extensive medical background, Tom entered the insurance world by way of employee benefits. He’s spent the last couple years broadening his knowledge by focusing on property and casualty. A Roseville native, Tom now resides in Edina with his wife Amber and children Cole and Charlotte and works primarily out of Flagship’s Edina office.
Tom loves being involved with his kid’s athletics, and being an active member of his church. Whether up at the cabin or acting as that embarrassing parent dancing in the car as he’s dropping his son off at middle school, he loves to have fun and laugh. He’s co-founder of a non-profit, and has led many medical mission trips to Haiti. He believes in helping others, which is why his favorite quote is, “What we do for ourselves dies with us. What we do for others and the world remains and is immortal.” – Albert Pine

Eileen Vasko

Agent

Learn More about Eileen
Eileen began her career in the insurance industry in 1986, providing customer service for an insurance agency in Bloomington, Minnesota. She took a brief hiatus in 1993 to raise a family but returned to the field in 1998. Eileen joined Flagship Insurance Services in 2013 as a licensed agent for sales and service of individual life and health products, including Medicare. Eileen also assists and advises small employers down to 2 employees who want to offer employee benefits. She is certified in the Private Health Insurance Market to find the best health solution for individuals and small employers. Eileen is a certified Notary Public.

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

Customer Service Representative

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

Customer Service Representative

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.

Annie Baide

VP Human Resources

Learn More about Annie
Annie joined Flagship Insurance Services in 2018 and brought a wealth of knowledge & experience to our Agency Management role. Annie graduated from Rasmussen Business College with a degree in Legal Office/Business Office Management in 2004. Since that time, she has worked in the Insurance Industry, with many years in Human Resources, Accounting & Office Management. Annie has a comprehensive knowledge of the insurance industry regarding Personal Lines, Farm, Life, Retirement plans, Health Insurance and Agency Management. Annie has achieved a CIC (Certified Insurance Counselor) designation as well as an Accredited Customer Service Representative designation in Personal Lines.

Jeffrey Jennings

Agent

Learn More about Jeff
Jeff services property and casualty clients around the St. Cloud area.

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.

Get In Touch

I am interested in these services

3 + 2 =

© 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