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 .

OUR TEAM
We are so excited for you to meet our team!

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.

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.

Winston
CCO (Chief Canine Officer)