Head Insurance Agency LLC

Head Insurance Agency LLC A family owned independant insurance agency located in Sherwood, Wisconsin. We are here to help you Our agency’s history dates back more than 60 years. to 5p.m.

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. The agency was started by Kenneth Head in 1947 and continues today with the third generation ownership at W579 Castle Drive Sherwood. We serve our customers in Wisconsin with au

to, home, farm, business, 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 8a.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.

As your family tree grows, the importance of strong roots does too. Life insurance can do just that, providing financial...
05/27/2026

As your family tree grows, the importance of strong roots does too. Life insurance can do just that, providing financial stability and emotional peace of mind as you expand your family tree through marriage, children, and more.

Whether you’re exploring your first policy or additional layers of coverage, we are here to help. Give us a call today for a personalized quote or coverage review.

With National Small Business Week here, we wanted to share some key insurance considerations for any small businesses na...
05/04/2026

With National Small Business Week here, we wanted to share some key insurance considerations for any small businesses navigating higher costs.

When budgets are tight, it might seem like a good idea to keep coverage lean, but being underinsured can cause devastating consequences. Here are a few risks of not having enough insurance:

✅ A loss can become an out-of-pocket event - If building, inventory, equipment, or tools are underinsured, you can end up paying the gap between what your policy covers and the actual cost to repair or replace the lost item(s) after a fire, theft, or storm, even if you “have a policy.”

✅ Income can stop, but bills keep coming - Property coverage can help offset repair costs in the event of damage. But without the right business income coverage, payroll, rent, and ongoing bills keep coming even when operations and cash flow have paused.

✅ Liability can spill past your limits - A single claim can bring legal defense costs, settlements, and medical expenses that exceed your limits, creating a significant financial burden.

If you have questions or are interested in adding additional coverages, give us a call. Our team can help find a solution that respects your budget and strengthens your long-term protection.

Myth or Fact – the IRS taxes life insurance benefits? 🤔 Today, we’re sharing the definitive answer. Swipe to learn more ...
04/21/2026

Myth or Fact – the IRS taxes life insurance benefits? 🤔 Today, we’re sharing the definitive answer. Swipe to learn more ➡️

As always, if you’re interested in exploring your life insurance options, do not hesitate to reach out. We are here to help!

Heavy-duty tools and machinery are the backbone of every jobsite, so it’s important to ensure your equipment coverage ke...
04/16/2026

Heavy-duty tools and machinery are the backbone of every jobsite, so it’s important to ensure your equipment coverage keeps pace with real-world risks. Swipe for key considerations to make sure your coverage is up to the task.

Need help tailoring your tools and equipment insurance? Give us a call today, and we will walk you through your options.

Christ the Lord is risen! May your spirits be lifted and your hearts filled with the warmth of God’s love. From our fami...
04/02/2026

Christ the Lord is risen! May your spirits be lifted and your hearts filled with the warmth of God’s love.

From our families to yours, Happy Easter!

Our office will be closed on Good Friday, April 3rd.

With the new year in full swing, it is essential to understand the emerging risks that could impact your business. Swipe...
03/26/2026

With the new year in full swing, it is essential to understand the emerging risks that could impact your business. Swipe to learn about two to keep top of mind.

Have questions about your current coverage or cyber preparedness? Call us today to ensure your business is protected.

March Madness is here — and while upsets make the tournament exciting, they’re not nearly as fun when it comes to your i...
03/16/2026

March Madness is here — and while upsets make the tournament exciting, they’re not nearly as fun when it comes to your insurance coverage! 🏀😅

Make sure your policies aren’t the ones getting knocked out early. If it’s been a while since you reviewed your coverage, now’s a perfect time for a quick full‑court checkup.

Need help with your game plan? We’re always here to assist — no overtime required. 😉

— Head Insurance Agency

Due to the inclement weather and travel conditions, our office will be **closed on Monday, 03/16**.If you need assistanc...
03/15/2026

Due to the inclement weather and travel conditions, our office will be **closed on Monday, 03/16**.

If you need assistance, please email **[email protected]** or leave a voicemail at **920‑989‑1473**. We’ll respond as timely as possible to your inquiries.

Stay safe out there — and hopefully you can find a way to enjoy the snow day! ❄️

In honor of Debunking Day on March 11th, we’re setting the record straight on some of the most common and costly insuran...
03/11/2026

In honor of Debunking Day on March 11th, we’re setting the record straight on some of the most common and costly insurance myths.

Swipe through to find out what’s fact, what’s fiction, and what you should really be doing when it comes to your home and auto insurance.

If you have any questions about your coverage, give us a call. We’re here to help.

Picture this: You come home to find your basement swamped with 3 inches of water and raw sewage. What now?Swipe ➡️ to di...
03/06/2026

Picture this: You come home to find your basement swamped with 3 inches of water and raw sewage. What now?

Swipe ➡️ to dive into the must-knows of protecting your home from unexpected and costly damage.

Let's keep your home safe and sound. For coverage options or questions about your current coverage, reach out to our team. We are always here to help.

Address

W579 Castle Drive
Sherwood, WI
54169

Opening Hours

Monday 8am - 5pm
Tuesday 8am - 5pm
Wednesday 8am - 5pm
Thursday 8am - 5pm
Friday 8am - 5pm

Telephone

+19209891473

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