Meet Our Staff

Dean and his wife Tracy are the owners of Head Insurance. Dean has been in the agency for over 30 years and uses all his knowledge and experience to help customers to the best of his abilities. Dean works with all lines of insurance but specializes in commercial, life, and health insurance.

Dean has a Bachelor’s Degree from the University of Wisconsin Madison. He takes pride in getting to know his customers, often meeting with them in the comfort of their own home. Dean guides his customers from the initial information gathering, to assessing their needs and finding the best options to fit their lifestyle, to assisting with any inquiries or claims and making sure the process goes as smoothly as possible.

Dean and Tracy have lived in the Stockbridge area their whole lives and raised a family with three children. Their oldest son TJ works in the agency since graduating from high school in 2012. They also have a set of twins (Hunter and Hailey) who live and work in the Fox Valley. Dean is an avid outdoorsman and enjoys spending time in the woods or on the lake fishing. They both also enjoy spending time with their family and watching sports.

Tracy and her husband Dean are the owners of Head Insurance. Tracy has been in the agency for over 30 years and uses all her knowledge and experience to help customers to the best of her abilities. Tracy works with all lines of insurance but specializes in personal insurance.

Tracy has been in the agency for over 30 years as well and is the third generation owner of the agency. Tracy handles most of the agency management and accounting while also being an expert in personal lines insurance.

In her free time she enjoys spending time with friends, family, and her grandchildren.

TJ is the fourth generation to be a part of the agency. He works in all lines of insurance. He has been a part of the agency since 2012.

TJ graduated from Viterbo University (LaCrosse, WI) with a degree in Business Administration while also playing on the basketball team. He loves meeting new people and assisting them with all of their insurance needs. While assisting his customers is his number one passion, he also manages the agency’s staffing, online presence, marketing, and helps out wherever he is needed.

TJ married his wife Marla and together they have two children. He resides in the Fond du lac area and spend as much time as he can outside and on Lake Winnebago.

Mellony joined Head Insurance in 2023. She has years of prior experience working at a direct writing insurance company and also with another independent agency. Mellony works closely with all of our personal insurance customers and does an excellent job finding the best coverage for all your assets at the most competitive pricing we can offer.
Mellony resides in Kiel and enjoys camping, spending time with her family, and riding her motorcycle in her free time.

Cindy joined the agency in 2021 and brings with her over 30 years of insurance knowledge that she will use to service customers to the best of her abilities.

Cindy and her husband Jerry reside in New Holstein and love spending time with their children and grandchildren.

Jarod joined Head Insurance in 2024. He is coming in to the industry from the Auto Service industry and is learning rapidly how to best service all of your insurance needs. Jarod grew up and lives in Mishicot and enjoys spending time with family and being outdoors in his free time.

Trish is the newest addition to the Head Insurance family. She is a long-time customer and has extensive experience working on the company side of the insurance industry as a Claims Representative. She brings her knowledge, experience, and bright personality to the front desk and looks forward to assisting all of you with your daily inquiries.

Tom is the agency’s Medicare supplement guru. He owned the agency until 2010 and has over 55 years of insurance experience. Tom also works closely with townships and fire departments.

Tom and his wife Alyce have two children, four grand-children, and a growing number of great-grandchildren and enjoy spending as much time with them as possible.