Who we are

Our associates are the most important part of our company

We became one of the most financially strong mutual insurance companies in the U.S. by striving to provide the best possible service to our business customers. We do this by having conversations, forming relationships, and getting to know the people we work with and their businesses.

We make that same commitment to our associates. When you join Sentry, we don’t just want you to perform tasks each day. We want you to enjoy your time with us. You’re in the driver’s seat of your career path here—sharing feedback, creating goals, accessing professional development resources, and identifying how you can contribute to both your success and the success of the company.

Yes, we work hard. But we work with the purpose of helping others, and with the understanding that there’s more to life than work. We invite you to learn more about us. You’ll find we’re much more than insurance.

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What we offer

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.

Growth opportunities

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.

Brands of Sentry

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.