We were raised with Midwestern roots and built on small-town values—ones we’ve carried with us as we’ve grown from a local vehicle insurer into a nationwide presence.
Our name pays tribute to our history, but our service tells the real story of who we are and where we come from. Because while we may be a business with a bottom line, you’re never just a number.
We promise to always treat you as a person—one who deserves the best service, no matter who you are or what stage you're at in life.
Experience you can trust
Real people to talk to
Service our customers value
The Hardware Dealers Mutual Fire Insurance Company of Wisconsin begins writing auto insurance for its members. Previously, the company sold property and casualty insurance to Wisconsin Retail Hardware Association members. That small business is now known as Sentry Insurance—the parent company of Dairyland.
Stuart Struck, a University of Wisconsin–Madison professor, forms Dairyland Mutual Insurance Company of Wisconsin. The company begins selling specialty insurance for drivers who can’t get standard coverage because of poor driving records, little experience behind the wheel, or no prior insurance.
Sentry acquires Dairyland, which at the time wrote non-standard auto policies in 27 states. Sentry also begins to insure riders and their motorcycles.
Looking to take the next step in your career? Join the Dairyland team! We offer competitive compensation, a hybrid work model, and strong benefits packages.
Stay up to date on the latest Dairyland news, announcements, and initiatives
*Dairyland® brand products are underwritten by a member of the Sentry Insurance Group. Sentry has an AM Best Financial Strength Rating (FSR) of A+ (superior), current as of June 2023. See ambest.com/ratings/guide.pdf for rating information.