Check out your Company Bowl for anonymous work chats.
At Sentry, we know your career path might change over time. That’s why you have numerous resources to help you grow professionally and personally no matter what direction your journey takes. Learn about our growth opportunities.

Growth opportunities
Being rated A+ (Superior) by AM Best for a 30th consecutive year means more than just being able to pay our customers’ claims. It’s a testament to our strong management team, to the decades of industry experience our employees bring to the table day in and day out, to the development of cutting-edge technology that provides our customers the best overall experience, and to a well-diversified business mix.

AM Best rates Sentry A+ 30th straight year | Sentry Insurance
Our community involvement goes beyond charitable contributions. Our associates lead the way, offering their time and support to worthy causes. Check out some ways we’re committed to helping improve our communities.

Community-minded
Congratulations to the college class of 2021! Are you looking for a satisfying career after graduation? To help get you started, check out jobs.sentry.com and follow our Sentry Careers social accounts for the latest employment opportunities.

Job Opportunities | Careers at Sentry Insurance
We’re proud of the job opportunities we can offer you as one of the financially strongest mutual business insurance companies in the U.S. Join our Talent Network to stay up to date on our current and future job openings.

Job Opportunities | Careers at Sentry Insurance
Even while working remotely, we help our associates remain engaged and healthy. Through our #WorkingBetterTogether intranet hub, our Health and Wellness team leads group stretches and fitness breaks, shares healthy meal options, offers activities to help de-stress, and conducts webinars on various health-related topics. Together, we stay connected and active.

What we offer
The hospitality side of our business is growing. Whether you’re looking for a summer job or new career, SentryWorld provides a warm, welcoming, team-focused atmosphere. Explore your options today.

The Inn at SentryWorld to create up to 125 jobs
We’re pleased to share we’ve finalized our conversion to a mutual holding company structure. As part of this conversion, our official name is now Sentry Insurance Company. Learn more in our news release.

Sentry converts to mutual holding company structure | Sentry Insurance
We’re thrilled to share that Deloitte has named Sentry as the 2020 winner of the Distinguished Performer Community award for our focus on giving back to the community. We feel we have a commitment and responsibility to improving the communities where we live and work, and our associates take the lead with their time and contributions. Please read more about this award and some of our recent community efforts.

Sentry wins Deloitte Wisconsin 75™ community award
We’re glad to be named a Forbes Best-in-State employer, because it means our employees feel Sentry is a great place to work and grow their careers. We highly value them and the critical role they play in building long-lasting relationships with our customers.

Forbes names Sentry one of Wisconsin's best employers | Sentry Insurance