Our Team

Dennis Cliff

PRESIDENT

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

OFFICE MANAGER/AGENT

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.

Kara Lechner

Account Manager

Kara started working for an Independent Insurance Agency in Florida back in 2000. She relocated to Wisconsin at the end of 2019, and she had not seen snow in over 20 years. After being hit with the many blizzards that pounded us with snow this last winter, she still says she loves it up here in Madison, and is enjoying learning about her new surroundings. The thing she likes most about working for Cliff Insurance Agency is that she knows our clients are well protected and she will be right there to help them if the unexpected happens.

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.