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.

If summer has you feeling like you have lost all concept of time and are never sure exactly what day it is anymore, we'v...
08/24/2026

If summer has you feeling like you have lost all concept of time and are never sure exactly what day it is anymore, we've got some good news to share... back-to-school season is here! And, with the season comes a return to structure, routine, and finally knowing the day of the week.

We hope the transition back to school is a smooth one for all of you. As always, please don't hesitate to reach out if there's anything we can be of help with as fall gets underway.

Tune in! Tomorrow, 8/11 at Noon!
08/10/2026

Tune in! Tomorrow, 8/11 at Noon!

We’re going LIVE again!

Join us Tuesday at NOON with Nathan from VKB Homes and TJ from Head Insurance as we answer more of your questions about insurance, repairs and what comes next after the tornado.

Haven’t watched the first one yet? Check it out, and drop your questions below for Tuesday!

07/27/2026

Our thoughts are with everyone affected by today’s tornado and severe storms. Our office currently doesn’t have any phones or internet service and we’re working to restore communications and support our team.

We know many families are dealing with damage and uncertainty. Our team is here to help, and we appreciate your patience as we work through a high volume of claims.

If it’s safe to do so, document any damage with photos, take reasonable steps to prevent further damage, and save receipts for emergency repairs. If you have vehicle replacement needs, most of our auto insurance companies provide 14 days of automatic coverage for newly acquired vehicles, so we can handle those updates after the immediate storm claims.

If you’ve experienced damage, please contact us when you’re able, and we’ll help guide you through the claims process.
Stay safe, and thank you for your patience as our community recovers.

Ever wondered whether auto insurance follows the car or the driver in Wisconsin? 🚗💭Here’s the quick breakdown:• In most ...
07/22/2026

Ever wondered whether auto insurance follows the car or the driver in Wisconsin? 🚗💭

Here’s the quick breakdown:
• In most cases, **insurance follows the vehicle** — not the person driving it
• If someone has your permission to use your car, your policy is usually the primary coverage
• Excluded drivers, unlisted household members, business use, ride‑share, and delivery driving can all change how coverage applies
• Strong liability limits matter, especially if you ever lend your vehicle or borrow someone else’s

Real-life example:
If you lend your car to a friend and they get into an accident, **your** auto insurance typically pays first. If you’re the one borrowing a vehicle, the car owner’s policy generally leads, with yours as secondary.

Because every policy has different rules, exclusions, and endorsements, understanding the details helps you avoid surprise gaps in coverage.

If you’d like a review of your auto policy or want to compare quotes, our team at Head Insurance Agency is here to help you stay protected on the road. 🚙🛡️

We’re excited to welcome a new faces to the Head Insurance Agency team! 🎉As our family-owned agency continues to grow, a...
07/16/2026

We’re excited to welcome a new faces to the Head Insurance Agency team! 🎉

As our family-owned agency continues to grow, adding great people helps us serve our clients even better. Please join us in giving a warm welcome to our newest team members Karyn & Scott— we’re thrilled to have them on board!

For more information, or if you would like to welcome them personally, find their bios and contact information on our 'Meet Our Team' page.
https://www.headinsurance.biz/our-team

The Hilbert 4th of July Parade was successfully celebrated with great attendance, marking 250 years of Freedom; we hope ...
07/05/2026

The Hilbert 4th of July Parade was successfully celebrated with great attendance, marking 250 years of Freedom; we hope everyone enjoyed a safe weekend 🇺🇸

Cue the fireworks, fire up the grill, and get ready for what might be the most ambitious birthday cake of all time. 🎂Ame...
07/02/2026

Cue the fireworks, fire up the grill, and get ready for what might be the most ambitious birthday cake of all time. 🎂

America turns 250 this year, which means 250 candles on the cake … so someone should probably alert the fire department.

However you’re celebrating the Fourth of July, we hope it’s filled with great food, good company, and a sky full of fireworks.

Our office will be closed on Friday, July 3rd, in observance of the holiday. We’ll be back and ready to help on Monday. Wishing you a safe and happy Fourth!

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.

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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