Careers

Own your future with Sentry Insurance.

Sentry Insurance is 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 4,000 strong, our associates bring together diverse backgrounds, experiences and skill sets to make Sentry who we are.

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. 

We invite you to explore the career opportunities that await you at Sentry.

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.

Learn More

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.

Learn More

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.

Learn More

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.

Learn More

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.

Learn More

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.

Learn More

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.

Learn More

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.

Learn More

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.

Learn More

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.

Learn More

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.

Learn More

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.

Learn More

Sentry’s Training 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 Training team helps Sentry associates realize their goals and take their careers to the next level.

Learn More