Our Team

Dennis Cliff


Dennis worked for Metlife Auto & Home for almost 10 years before purchasing the Wilson-Boylan Insurance Agency in 2003. He lives in Middleton, with his wife and 2 daughters. Dennis enjoys hunting and fishing in his free time.

Nick Eifert


Nick has been with the agency since June 2003. Nick and his wife, Leah, have spent their entire lives in Verona. They have two children Nicholas & Isaac. Nick has excelled in serving his clients with fast and efficient service.

Karen Barger

Account Manager

Karen started her insurance career in 1989 as an agent assistant in Neillsville WI where she born and raised. She has been in the insurance field ever since. Karen and her husband, John live in Fitchburg WI. They both love the outdoors. In 2011 Karen and John founded Fisher Valley Felines, a Non-Profit, No-Kill Foster-based Cat and Kitten Rescue. When Karen isn’t at work she is giving cats & kittens a 2nd chance at life by finding them forever homes.

Brad Flory

Account Manager

Brad was born and raised in Toledo, Ohio and has been in the insurance industry for 30+ years. Brad started out his career in his family owned Insurance Agency in Toledo, Ohio. Brad lives with his significant other Lynn and they have two children together Ryan and Jonathan. Brad enjoys sports and fantasy football in his free time. Brad offers his many years of knowledge and service within the insurance industry.

Debby Ninmann

Account Manager / Agent

Debby began her insurance career in 1989 working as an Office Assistant. In her spare time, she enjoys fishing, reading, gardening, and spending time with family and friends.

Brittany Brisky

Account Manager / Agent

Brittany started her insurance career in 2017 with American Family. She has been with Cliff Insurance since 2019. She lives in Fitchburg with her partner, their dog, their cat, and their chinchilla. In her free time, Brittany likes to be outdoors (hiking, camping, fishing, you name it!) or inside playing videogames and catching up on her favorite shows.