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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, Inc, 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.

Cliff Insurance Family Photo

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.

An Independent Advantage

We are Independent Agents in Madison, Wisconsin, free to choose the best carrier for your insurance needs. We do not work for an insurance company; we work for you. We work on your side when you have a loss and follow through to see that you get fair, prompt payment and service. Cliff Insurance Agency, Inc represents a carefully selected group of financially strong, reputable insurance companies. Therefore, we are able to offer you the best coverage at the most competitive price. What is an Independent Insurance Agent? When you decide to buy a car, you wouldn't purchase the first one you see. What if one day the automobile industry decided to make only one type of car, one make and one model. You wouldn't have a choice! The same situation holds true for insurance. You need insurance to drive a car, to purchase a house, to protect your family's financial future and to run a small business. But if there was only one insurance company that offered only one type of insurance, you wouldn't have a choice. The only solution would be going to that one company. With an independent insurance agent, you have choices. Independent agents are not tied to any one insurance company. One of the advantages of using an independent agent is that he or she works to satisfy your needs. You are using an expert for an important financial decision. An independent agent has several companies that he or she can approach to get you the best coverage at the best price. And your independent agent will know the companies with the most efficient claims departments to recover your losses as quickly as possible. When you buy insurance, you want an advocate who will properly assess the risks you face and give you an objective analysis of the marketplace, because it's up to you to make the final choice.