Skip to the content

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.

Jacob Christensen Headshot

Jacob Christensen

Account Manager

Jacob was born and raised in Green Bay, Wisconsin, and has recently moved to the Madison area. Before coming to Cliff Insurance, Jacob worked for American Family Connect for over 5 years and loves to help people with his excellent customer service skills. He enjoys all types of sports and likes to disc golf and snowboard in his free time.

Mariah Sherry Headshot

Mariah Sherry

Account Manager

Just a small-town girl meant for the city world. I was born and raised in a small town in Northern Wisconsin. My boyfriend and I have been together since high school and we moved to the Madison area about 10 years ago. Our little family consists of our two fur-babies, Loki and Remi, and our sassy but sweet leopard gecko named Bellatrix, however, we hope our next addition to the family will be a kiddo! Some of my favorite things to do are being outside, reading, watching documentaries, exercising, and spending time with my family. I challenge myself is to be 1% better every day and I am incredibly blessed to have found a career that I am so passionate about and find so much purpose in.