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Meet Our Staff

As our client, you will have a team of highly qualified professionals working for you to provide you with the best coverage for you, your family, or your business.  Building a long-lasting relationship with our clients is our number one priority.

Dennis Cliff

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

Nick Eifert

Office Manager

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.

Brad Flory

Brad Flory

Senior 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.

Bret McGuire

Bret McGuire

Account Manager

Bret has spent over 20 years in the client management and customer service fields. He enjoys helping people find the right solutions with efficient, courteous service. Born and raised in Madison, he loves his city and all the sports associated with this great state. In his free time, Bret loves exploring live ‘60s and ’70 music and building military models.

Brittany Brisky

Brittany Brisky

Account Manager

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 video games and catching up on her favorite shows.