Madison, WI

At Sentry Insurance, we’re proud to call Stevens Point, Wisconsin our home. And we’re proud to extend our roots beyond Stevens Point to Madison.

As Wisconsin’s capital and second largest city, Madison combines abundant natural beauty, friendly communities, great schools, diverse cultural opportunities and a host of modern amenities. In short, the Madison area is a wonderful place to live, work and play. It’s no wonder Madison consistently ranks as a top community by organizations like USA Today, Huffington Post, Smartgrowthamerica.org and Bicycling Magazine, among countless others.

To learn more about all that Madison offers, click on the links below:

A capital city with endless opportunities.

Nestled in the south central part of the state, Madison is less than two hours from our home office in Stevens Point and only a short drive from Milwaukee and Chicago—making travel to and from the area quick and convenient.

And once you’re here, you’ll see why Madison captures so many accolades and rankings that cements the city as one of the best places to live, work, play, and raise a family. From endless opportunities for year-round recreation, award-winning dining, entertainment, and the arts, to top-rated schools, affordably-priced housing, and clean, safe communities, there are plenty of reasons to consider joining Sentry Insurance and making Madison your home.

Our presence continues to grow in Madison—our Personal Lines Madison office is home to more than 175 associates as well as a number of consultants. The facility itself is in a beautiful area with great access to walking, biking, shopping and dining, and is equipped with all the latest in modern office technology, making it easy to work and connect with other Sentry associates across the organization. Downtown Madison is home to the hub of our IT co-op program. And we’ve also opened a Regional business unit office on Madison’s northeast side.

We invite you to take some time to explore all that working at Sentry and living in Madison has to offer.

Jobs in Madison, WI

Our Location



Madison, WI Office
1800 Deming Way, Suite 400
Middleton, WI 53562
608-836-3000

IT Coop, Madison
100 State Street, Suite 2
Madison, WI 53703
608-836-3000