Brands of Sentry

Sentry Insurance

In 1904, members of the Wisconsin Retail Hardware Association gave us our start when they formed their own mutual insurance company. We’ve grown far beyond Wisconsin and the hardware industry in the years since. But we’ve always retained our core values as a mutual company.

We’ve never forgotten our Midwest roots, either. Our true strength comes from our dedication to personalized care—something we’ve provided since our inception. We grew by leveraging knowledge in one market to branch out into similar industries.

We work hard to understand our customers’ businesses—and their industries—inside and out, and we work hard to build long-term relationships. Our current mix of customers is a testament to our broad knowledge. And we put that knowledge into practical use to serve our customers better, offering services to minimize risks in the workplace and providing assistance when something unfortunate happens.

Today, we’re one of the largest and strongest mutual insurance companies in the nation. We hold this position largely in part to our dedicated associates. More than 4,200 strong, our associates bring together diverse backgrounds, experiences, and skill sets to make Sentry who we are.

We’re known for our high retention rate, community support, and personal and professional growth opportunities. Learn more about us and what we can offer you.

Careers at Sentry

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Sentry Insurance

The Sentry Insurance brand includes a large portion of our business insurance coverage. Our strength in this area lies in our dedication to personalized care.


Our Dairyland brand encompasses Dairyland Auto® and Dairyland Cycle®, offering non-standard auto insurance and coverage for motorcycles and motorcycle riders, respectively.


Associates within our Hortica brand have been serving the horticultural industry for more than 130 years, bringing their specialized experience and service to our customers.


You may know SentryWorld as Wisconsin’s premier parkland golf course. But it’s also home to a soon-to-be-completed boutique hotel, two popular restaurants, and world-class facilities for weddings, holiday parties, banquets, meetings, and other events.