Welcome to Head Insurance Agency, your local Independent Insurance Agency able to handle all your personal and business insurance needs. Our mission is to review your needs and provide the best value and service possible. Our agency’s history dates back more than 75 years. The agency was started by Kenneth Head in 1947 and continues today with the fourth generation ownership at W579 Castle Drive Sherwood.

We serve our customers in Wisconsin with auto insurance, homeowners insurance, farm insurance, business insurance, life and health insurance products. We currently represent more than 20 top rated companies which are able to provide all types of protection for our individual customers needs.

Our licensed staff have an average of 20 years experience serving the needs of our clients. At Head Insurance Agency the customer always comes first. We are available Monday thru Friday 8 a.m. to 5 p.m. other times by appointment. We love house calls! Our goal is to make your insurance experience as comfortable as possible and give you the service and value you deserve.

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9 Tips to Boost Employee Morale

Posted: May 30, 2023

For business owners, hiring and retaining good employees is always a challenge. But in today’s highly competitive job market, the task of keeping your workforce engaged and productive is harder than ever.After a disruptive few years following the COVID-19 pandemic, more and more working Americans find themselves dissatisfied with their current job. In fact, a recent poll from Monster.com found that an astounding 96% of...

Growing Your Business: 9 Tips for Opening a New Location

Posted: May 30, 2023

You started your business with a dream. A vision for the future. And there’s no satisfaction like watching that dream come to fruition.If business is booming and all your hard work is finally paying off, it’s natural to think about expansion. But how do you know when the timing is right to open a new location?The truth is, there can be danger in growing your...

Your Guide to Memorial Day

Posted: May 26, 2023

While Memorial Day is often a day marked by grilling, spending time with family and celebration, it’s true meaning is a bit more somber. This national holiday honors all soldiers who have died while in service to the nation. In more recent years, we also honor all those in the United States military.Before you hit the water and break out the sparklers, pause to remember...

Head Insurance Agency, LLC specializes in auto, home, business, and life insurance.

Insuring Sherwood and All of Wisconsin

Specializing In Erie Insurance

Specializing In Erie Insurance

Recent News & Updates

9 Tips to Boost Employee Morale

Growing Your Business: 9 Tips for Opening a New Location

Your Guide to Memorial Day