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 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.
Brad Flory
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.
Mariah Sherry
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.
Thomas Oberg
Born and raised in central Wisconsin, Tom is a true Wisconsinite at heart and has lived in the Madison area for nearly 30 years. Blessed with a large family of siblings, nieces and nephews he enjoys being with them as often as possible. He also enjoys spending time outdoors and has a wide range of reading interests. Tom had a 40 year career in the computer information systems industry and looks forward to serving clients’ insurance needs.
Butch Rieke
Raised in the Midwest Butch lived in Arizona for the last 20 years. He moved back to Wisconsin to be near his family. Butch loves football, basketball and other outdoor activities. He was a licensed insurance agent in Arizona for 20 years and looks forward to assisting clients with their insurance needs.
Kayla Meister
I was born and raised in Mt. Horeb and I have an associates degree in Criminal Justice. I have a German Shepard rescue named Harley. I love to read, spend time with friends, and be outside and active as much as I can! I’ve always been a helper and I strive to learn something new every day. I am excited to start a new chapter here at Cliff Insurance and build a great relationship with our insureds!