Cliff Insurance Agency: A Tradition of Quality & Integrity

Welcome to Cliff Insurance Agency, your home for traditional quality and integrity. Since 1956, we have been dedicated to serving Wisconsin residents and businesses with the best in insurance products and advice. We'd like to count you among our valued clients for auto insurance, homeowners insurance, life insurance, umbrella insurance and business insurance.

Our History of Service

In 2003, the Wilson-Boylan Agency became Cliff Insurance Agency, signifying a change in ownership but continuing a decades-old tradition of excellence. When I put my name on this agency, I made a pledge to the residents of the Middleton and Madison, Wisconsin area that we would live up to the highest standards, and I can proudly say we uphold that pledge daily.

As an independent insurance agency, we represent multiple companies, allowing our clients more choice and more competition for their business. That means we can provide policies tailored to your individual needs at prices that fit your budget. Our insurer partners include Progressive Insurance, AAA Insurance, Hastings Mutual Insurance, Wisconsin Mutual Insurance, IMT Insurance, Wilson Mutual Insurance, and Kemper Insurance.

Personal Attention

At Cliff Insurance Agency, each client is treated as a unique case. There are no cookie-cutter approaches. You can expect the absolute best from us whether you need personal insurance or business insurance.

We work directly with you to unveil risks and select from a wide menu of protection solutions. We have grown 300% in nine years as a result of our expertise and personalized approach. Referrals from happy clients drive our growth.

At Cliff Insurance, your phone calls will be answered by a real-live person during business hours—no phone system that doesn't help you and no service staff that can't answer policy questions.

Come meet us at Cliff Insurance and see what a difference great products and superior service can make!

- Dennis Cliff