About Us


Since the beginning of our insurance agency in 1956, we have built a reputation for honesty, integrity, and dedication to protecting our customers’ peace of mind through sound financial protection.

Dennis Cliff purchased the former Wilson-Boylan Agency in 2003, bringing his ten years of experience as a direct writer for Met Life. Cliff Insurance Agency, which is based in Middleton, Wisconsin and serves the Madison area, is built on a 50 plus-year tradition of excellence, a standard that we continue to live up to.

Independent and Comprehensive

As an independent insurance agency, we can offer our customers the coverage they need. With more companies to choose from, we can find the coverage that works best for you, along with the competitive pricing our customers have come to expect from us. From auto to homeowners to life and business, we can meet all your insurance needs.



Because we are a customer service focused, independent insurance agency, we are always able to give our customers personal, individual service. We want to be there for our customers, their families and their businesses today and tomorrow, helping them adapt to their diverse and changing needs.