When you live or work in the Hudson Valley, you want insurance that fits your life-without the runaround. That's where we come in. From renters & homeowners to contractors & small businesses, we help you protect what matters most with affordable, reliable insurance solutions you can count on year after year.

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Personal Insurance

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Commercial Insurance

Head Insurance Agency

Your Local Insurance Experts in Sherwood, WI

Serving Sherwood & the Fox Valley with Personal, Business, and Life Insurance

As an insurance agency Sherwood WI, Head Insurance Agency serves families and businesses across the Fox Valley—Appleton, Green Bay, Oshkosh, and Fond du Lac—within about 30 miles of our office by High Cliff State Park on Lake Winnebago. From everyday protections to specialty coverage, our team helps you compare options quickly, with one call for personal insurance, comprehensive business insurance, and trusted life insurance guidance.

Why Choose Head Insurance Agency?

Head Insurance Agency is a fourth generation family-owned, independent insurance agent Wisconsin customers rely on for friendly advice and fast follow-through. As an independent agency, we work with multiple carriers to find value without sacrificing coverage. Clients tell us they appreciate one-stop convenience, proactive policy reviews, and a real person answering the phone. Located near High Cliff and the Lake Winnebago shoreline, we understand regional weather, commuting patterns on I-41, and community needs from Sherwood to the greater Fox Valley.

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Personal Insurance

Home, auto, renters, landlords, umbrella & more



Explore Commercial Insurance
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Commercial Insurance

Reach out to us or request a personalized quote



Explore Life Insurance
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Life Insurance

Choose the right life insurance—term, whole, or universal



Explore Commercial Insurance
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What Our Clients Say

Client Testimonials & Reviews

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TJ and the team at Head Insurance have been wonderful to work with over the years. I have gone to them for probably the past 20 years. I have had home insurance, auto insurance, renters insurance, and boat insurance through them. They have always given me the best rates and are so personable, helpful and reliable. I have referred many of my friends and family to Head Insurance, and will continue to do so for many more years. Thank you for all you do and for all of your help over the years!


- Beth Nettekoven

Everyone at Head Ins. Agency is great! They are always looking out for me and making sure that I am getting the best coverage for our family and all the things that we have. I highly recommend them for all your insurance needs!!!!


- Lorne Andrews

We always give TJ a call when our policies are up for renewal to see if he has any recommendations. He has offered several great suggestions over the years, and I would encourage everyone to do the same. He is very knowledgeable and quick to get us a response! Very glad to have him as our Agent!

- Mike Loomis

Due what was being reported as "Standard inflation" rate increases with the tradition big name insurance companies, I was directed to TJ at Head Insurance. He helped me put together new insurance coverage across the board saving me over 30% of the renewal prices. Thank you TJ for the great service!

- Nick Gilbertson

The customer service from Cindy at Head Insurance has been excellent. I had an issue of my parents' policy and she has been very informative and helpful. If the rest of the staff is like her it is the insurance agency to choose.

- Sara Parise

When I started working with TJ I realized how much I didn't know. After he took the time to explain it to me. I trust TJ and his team. He protects everything of mine. My business and all our personal insurance needs. If it wasn't for TJ, my business would not be doing as well as it does.

- Patrick Muller

A Selection of Trusted Carriers We Work With

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Our Carriers

Serving your community

Proudly serving Sherwood, Appleton, Green Bay, Oshkosh, Fond du Lac, and nearby Fox Cities neighborhoods—Grand Chute, Menasha, Neenah, De Pere, and Ashwaubenon. Ask about local considerations like winter driving, lake-area homes, sump pump/water backup, and seasonal toys from pontoons to sleds.

Answers to common insurance questions

  • What types of coverage can I get through Head Insurance Agency?

    Home, auto, umbrella, renters, condo, valuables, motorcycles, boats, RVs, business coverage (BOP, liability, property, auto, workers’ comp, cyber, professional liability), and life insurance options.

  • How do I request an insurance quote?

    Start online with the form and we’ll call to confirm details, or phone us directly for immediate help.

  • Which areas do you serve?

    Within ~30 miles of Sherwood across the Fox Valley—Appleton, Green Bay, Oshkosh, Fond du Lac—and throughout Wisconsin.

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Get Started

Get a Quote or Contact Us

Prefer to start online or by phone? Use our detailed form for faster quotes—phone number required so our team can follow up with the right questions—or call to speak with a local agent. You’ll get clear options and next steps, whether you need one policy or an entire program for your household or company. For quick answers, contact us and we’ll respond promptly during business hours.