Head Insurance Agency LLC

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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 auto, 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.

October is Breast Cancer Awareness Month, making it the perfect time to review a few key facts and statistics about earl...
10/06/2026

October is Breast Cancer Awareness Month, making it the perfect time to review a few key facts and statistics about early screening. Breast cancer remains one of the most common cancers in the U.S., and early detection through routine screenings can make a meaningful difference.

Swipe for a few important facts and statistics to keep in mind.

As a reminder, many health insurance plans cover preventive screenings at little or no cost, making it easier to take an active role in your health. And, if you're not sure whether your plan covers preventive breast cancer screenings, our team is happy to help. Please do not hesitate to reach out with any questions.

09/29/2026

On November 1st, daylight saving time ends, and the clocks fall back an hour. This shift not only gives us an extra hour of much-needed sleep but also serves as a timely reminder to take care of a few things around the house as we approach winter.

So, that said, here is a quick home checklist worth running through as the days get longer:

✅Turn back any clocks that do not automatically adjust themselves before bed on Saturday night.

✅Test and replace the batteries in your smoke and carbon monoxide detectors. This is one of the easiest ways to keep your household safe heading into winter.

✅Check your outdoor and security lighting. As daylight hours get shorter, having well-lit outdoor spaces can be a key safety step.

Taking care of these small to-do list items can make a real difference in how safe and prepared your home feels all season long.

As always, if there is anything we can assist with, do not hesitate to reach out. We are here to help.

This Life Insurance Awareness Month, we want to highlight an unfortunate reality: too few Americans have adequate life i...
09/09/2026

This Life Insurance Awareness Month, we want to highlight an unfortunate reality: too few Americans have adequate life insurance. The good news is that there are several simple steps you can take to better protect your family’s future.

Swipe for key statistics and steps to consider. As always, we are here to help ensure you have the right life insurance protection. Reach out today for assistance with any of the steps we’ve recommended or to further explore coverage for your family.

Happy Birthday to our owner/advisor, TJ! 🎉🎂We’re grateful for the leadership, dedication, and care TJ brings to Head Ins...
09/04/2026

Happy Birthday to our owner/advisor, TJ! 🎉🎂

We’re grateful for the leadership, dedication, and care TJ brings to Head Insurance Agency and the clients we’re proud to serve.

Please join us in wishing TJ a fantastic birthday and a great year ahead! 🎈

Labor Day is all about celebrating the workforce, and the best way to honor hard work is to take a real break from it. S...
09/03/2026

Labor Day is all about celebrating the workforce, and the best way to honor hard work is to take a real break from it. So to celebrate, our team is fully committing to the cause by penciling some cat naps into our schedules this weekend.

A quick heads-up: The office is closed on Monday, September 7th. We will be back on Tuesday, September 8th — recharged, refreshed, and ready to get to work.

We hope you have a long weekend full of good food, good company, and zero emails!

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

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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