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ABOUT

We are so happy that you have an interest in who we are here at Winston Insurance Group! Family means everything to us, and we will protect our children's futures in every way we can.  We knew that we had to help others secure their futures too! Our goal is to help anyone we can gain the peace of mind that insurance can bring. No one wants to be stuck in a financially devastating situation or leaved their loved ones to pick up the pieces either. 

You may have wondered why there is a dog in our logo? Well, part of our family includes our dog, and muse, Winston. He signifies family, strong bonds, happiness, and home to us. So, what better way to bless our business than with the very dog who signifies our most important values . 

Photo of the Winston Insurance family holding theri dog Winston

OUR TEAM

We are so excited for you to meet our team! 

Portrait of Cindy Kiley Craig
Cindy Kiley-Craig

Medicare 

Health / Dental / Vision

Life 

Mortgage Protection

Long Term Care

State License # 17269072

Executive Board Member with Lasting Mark

I help people navigate the confusing world of Medicare and Health insurance, making sure you have the right coverage in place without overpaying. Not only will I get you the best coverage, I'm your local rep ready whenever you need me. 

Portrait of Jason Craig
Jason Craig

Retirement Planning 

Securities 

Market-Safe Investments

Income Planning

Life Insurance

State License # 19260503

Executive Board Member with Lasting Mark

I help retirees plan long, successful retirements with strong income plans, tax strategies, market-safe growth, and plans for "what if."

I help all families, whether working or retired, protect their future with financial strategies that provide cash benefits, tax advantages, guarantees, and peace of mind. As an independent advisor and broker, I work for you — not for the insurance companies. 

Portrait of Winston
Winston

CCO (Chief Canine Officer)

Phone

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34 Schroeder Ct, Ste 260

Madison, WI 53711

 

We are not connected with or endorsed by the United States government or the federal Medicare program.

 

We do not offer every plan available in your area. Any information we provide is limited to those plans we do offer in your area. Please contact Medicare.gov or 1-800-MEDICARE to get information on all of your options.

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