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.

Backyard fun is one of the best parts of a Wisconsin summer — but features like pools, trampolines, and play equipment c...
06/24/2026

Backyard fun is one of the best parts of a Wisconsin summer — but features like pools, trampolines, and play equipment can bring added liability risks for homeowners.

A few things to keep in mind:
• Certain backyard features may require fencing, safety nets, or other protections
• Some items (like trampolines) may have coverage restrictions depending on your insurance carrier
• Regular inspections, maintenance, and documentation can make a big difference if a claim ever occurs
• Higher liability limits or an umbrella policy can help protect your finances in the event of an accident

If you’re adding or updating backyard features this year, it’s a great time to review your homeowners policy and make sure you’re fully protected.

Our team at Head Insurance Agency is always here to answer questions and walk you through your coverage options.

Stay safe and enjoy the sunshine, Wisconsin! 🌞🏡

Every June 14th, we celebrate the Stars and Stripes on Flag Day. While we’re all familiar with the United States’ flag, ...
06/14/2026

Every June 14th, we celebrate the Stars and Stripes on Flag Day. While we’re all familiar with the United States’ flag, we might not know all of the history behind this symbol.

To celebrate, we wanted to share a few fun facts about the history of the flag that might surprise you:

🔹 The current 50-star design was created by a 17-year-old. Robert G. Heft of Lancaster, Ohio, submitted the design as a high school project in 1958. It was chosen by President Eisenhower out of more than 3,000 submissions in 1960.

🔹 There have been 27 official versions of the flag. Twenty-five of those changes were solely to update the number of stars every time a new state joined the Union. The star additions were admitted on July 4th, and, together, they give us a rich visual history of the country's growth over time.

🔹 The colors for the flag have taken on their own meanings over the years. Charles Thomson, secretary of the Continental Congress in 1774, suggested that red represents hardiness and valor, white symbolizes purity and innocence, and blue stands for vigilance, perseverance, and justice.

🔹 Six American flags have been planted on the moon. Neil Armstrong and Edwin E. “Buzz” Aldrin were the first, but five additional Apollo missions have also left a flag on the lunar surface.

🔹 The current design is the longest-running version in history. No new states have been added since Hawaii joined the union in 1959, making this the most enduring flag design the country has ever had.

Wishing you a wonderful Flag Day filled with pride and appreciation for the history behind the flag we share.

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.

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

Website

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