Who we are

Our associates are essential to our success and our Total Rewards. We provide resources to help you grow while giving you time to enjoy your family and community. Learn more about us.

The benefits of working at Sentry go beyond a paycheck. Our Total Rewards include an 8% 401(k) company match with immediate vesting, volunteer time off, and opportunities for continuous learning and career growth. Learn more about us
Our community involvement goes beyond charitable contributions. Our associates lead the way, offering their time and support to worthy causes. Learn more about us.
At Sentry, we offer more than jobs. We offer careers. Our associates have numerous resources to help them grow professionally and personally. Learn more about us.
Our Sentry Insurance brand includes a large portion of our business insurance operation. Our strength in this area lies in building relationships and our dedication to individualized service.

Careers

Whether you’re new to the job market, looking to advance your career or are a seasoned professional, we offer an array of rewarding career opportunities across a variety of functions, from information technology, claims, sales and underwriting, to marketing, human resources, finance and more.

Sentry Insurance is dedicated to being there for our customers when they need us most. Our quick-thinking, knowledgeable Customer Service associates are committed to providing outstanding service and support to all of our customers.
Sentry Insurance is rooted in being there for our customers when they need us most. Our quick-thinking, customer-oriented Claims associates are on the front lines delivering on our promise, providing outstanding service and supporting our customers in their time of need.
Sentry Insurance is dedicated to the development of our technology staff and investment in our information systems. Our Information Technology associates play a critical role in our business, developing and maintaining an array of applications and technology across the company.
At Sentry Insurance, we make a powerful promise to all of our policyholders—to be there when they need us most. As a Sentry Sales associate, you have the opportunity to sell something more than just a product and be part of something more than just a business.
Sentry’s Underwriting associates play a critical role in our core operations, analyzing the risks and exposures of prospective insurance customers to support all of our company’s business segments.
Along with being one of the nation’s largest and strongest mutual insurance companies, Sentry Insurance also owns and operates a dynamic hospitality and dining operation, including PJ’s – SentryWorld and more. Our enthusiastic, service-oriented associates provide all of our guests with a first-class experience, whether they’re dining at PJ’s – SentryWorld, attending a wedding or event.
We truly are more than insurance. Sentry Insurance also owns and operates SentryWorld, the Midwest’s premier parkland golf experience and one of the area’s most dynamic event, recreation and dining venues. Sentry’s home office is also home to @1800, featuring fine dining as well as a stylish lounge, gallery and theater.
If you’re a hard-working, career-minded student looking for a bright future, an internship with Sentry Insurance might be the right fit for you. Sentry’s paid internships provide students with practical experience in real-world, real-work situations.
Sentry’s Corporate Learning associates are essential to our organization, helping our associates unleash their individual talents and thrive in their work systems. From facilitating instructor-led training sessions to growing and managing a robust library of interactive learning and organizational development resources, our Corporate Learning team helps Sentry associates realize their goals and take their careers to the next level.
Sentry’s Human Resources associates play a critical role throughout our organization, helping all of our associates on their journey from before date of hire on into retirement. From recruitment, onboarding and benefits enrollment to employee relations, development, policy creation, support and everything in between, our HR team helps Sentry associates navigate the abundance of information available at their fingertips.
Sentry’s leading-edge Investments team works tirelessly to manage all aspects of our investment discipline and portfolio—from initial strategy, research and analysis to real-time execution. Our Investments group is essential to Sentry’s overall strength and success, both short and long-term.
Sentry’s first-class corporate Marketing department works to manage and raise the profile of Sentry’s brands through the creation and execution of innovative, effective marketing plans and tactics for all of our business segments. Our Marketing group is comprised of five teams: Brand Marketing, Corporate Communications and Content, Creative, Customer Research and Digital Marketing.
Sentry Insurance has been protecting our policyholders for more than 100 years, and our protection spans beyond insurance alone. Our proactive, knowledgeable Safety Services associates help our customers save lives, time and money.

Our locations

At Sentry Insurance, we’re proud to call Stevens Point our home. And we’re equally proud to have 10 field offices located throughout the U.S. Our offices have been carefully selected—the communities in which we live and work have high standards, embrace cultural diversity, offer friendly, safe neighborhoods, provide quality education and boast a variety of entertainment, lifestyle and recreational activities.

At Sentry Insurance, we are proud to call Stevens Point, Wisconsin our home. With its convenient central location, breathtaking natural landscape and host of modern amenities, the Stevens Point area is a wonderful place to live, work and play.
Davenport is the largest of the cities that makes up the Quad Cities and combines natural beauty, friendly communities, great schools, abundant entertainment opportunities and a host of modern amenities. In short, the Davenport area is a wonderful place to live, work and play.
Affectionately known as “Pretzel City, USA,” Freeport is the largest city in Stephenson County, Illinois. Freeport combines natural beauty, friendly communities, great schools, abundant entertainment opportunities and a host of modern amenities.
The city of Goldsboro is famous for the best barbeque in eastern North Carolina—among other things. Goldsboro combines natural beauty, friendly communities, great schools, abundant entertainment opportunities and a host of modern amenities.
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.
Alabama’s state capital and second largest city, Montgomery combines rich history, abundant natural beauty, friendly communities, great schools, endless entertainment opportunities and a host of modern amenities.
Virginia’s state capital and fourth largest city, Richmond combines rich history, abundant natural beauty, friendly communities, great schools, endless entertainment opportunities and a host of modern amenities.
Affectionately dubbed “The West’s Most Western Town,” Scottsdale combines abundant natural beauty, friendly communities, great schools, diverse cultural opportunities and a host of modern amenities.
Westford is steeped in history and combines abundant natural beauty, friendly communities, great schools, a variety of recreational and entertainment opportunities and a host of modern amenities.

College students

If you’re a hard-working, career-minded student looking for a bright future, a paid internship or co-op program opportunity with Sentry Insurance might be the right fit for you. Sentry’s student-specific programs provide you with practical experience in real-world, real-work situations.

If you’re a hard-working, career-minded student looking for a bright future, an internship with Sentry Insurance might be the right fit for you. Sentry’s paid internships provide students with practical experience in real-world, real-work situations.
Get insider information on all our internship program offers straight from actual interns. Check out our Intern Insights!
Looking for a unique co-op experience? As part of our co-op program, you can join a select group of college students who get to make a real impact while working in a modern, collaborative space exclusively for co-op participants.