Sentry Careers
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Business insurance company offering multiple career paths, great benefits, and hybrid work model.
Sentry Insurance—founded in 1904 and part of one of the largest and most financially secure mutual insurance groups in the U.S.—is headquartered in Stevens Point, Wisconsin. We also have more than 20 offices located across the country that serve key markets. With assets of $29.8 billion and a policyholder surplus of $8.6 billion, Sentry is rated A+ (superior) by AM Best, the industry’s leading rating authority.*
Our employees drive our continued success:
Our products and services are made possible by a dedicated team of employees, many of whom have been with us for decades. More than 2,000 associates in Stevens Point—and another 4,000 around the country—work each day to help our policyholders prepare for the unexpected and plan for the future. We believe in supporting our employees in all phases of their lives, offering a comprehensive benefits package, hybrid work model, volunteer time off, and a positive work/life balance. We’re proud to be listed amongst:
• Forbes America’s Best Midsize Employers
• Forbes Best-In-State Employers
• Forbes Best Employers for New Grads
• Newsweek America’s Greatest Workplaces for Women
• Newsweek America’s Greatest Workplaces for Diversity
• Times America’s Best Companies – Midsize
Explore our current job openings. You’ll find numerous career paths available for all experience levels.
*Assets and policyholder surplus are as of Dec. 31, 2025, and represent the aggregate total for all members of the Sentry Insurance Group and are not reflective of any individual underwriting company. Sentry has an AM Best Financial Strength Rating (FSR) of A+ (superior), current as of June 2025.
And that’s a wrap on another successful campaign. Check out these photos of associates across the country doing their best to make dreams come true in the communities we call home!
The Magic of Giving, Making Dreams Come True: https://bit.ly/4hxfSH4
09/28/2026
This week, we’ll be at career events at UTEP - The University of Texas at El Paso, Michigan Technological University, El Paso Community College, East Carolina University, University of Wisconsin-Eau Claire, University of Wisconsin-Whitewater, UW-Oshkosh, University of Wisconsin-La Crosse, University of Wisconsin Milwaukee, Appalachian State University, and University of Wisconsin - Madison.
Join us at upcoming job fairs! https://bit.ly/47gP8FZ
09/24/2026
Planning to attend a career fair this fall? Make sure you’re prepared to connect and impress with these tips from our Talent Acquisition team.
Tips to land the internship: https://bit.ly/4rvaqJo
Have a great school year!
Class is back in session—learn to apply your skills with a hands-on internship with Sentry. Check out the internship page to apply for your Summer 2027 experience. https://bit.ly/4A3r1HX
09/21/2026
Join us at upcoming job fairs!
This week, we’ll be at career events at UW-Stout Polytechnic, Fisk University, University of Wisconsin-Madison, UW-Stevens Point, University of Wisconsin-Platteville, Middle Tennessee State University (MTSU), Tennessee State University, UTEP - The University of Texas at El Paso, Drake University, and Quad Cities' Colleges.
Get all the details by visiting our Events page: https://bit.ly/4rf2Ja1
09/16/2026
At Sentry, we’re in the business of relationships and conversations. That’s why we offer so many of our interns full-time positions, and why almost 80% of Sentry interns join the team.
More than 75% of Sentry interns are offered full-time positions: https://bit.ly/4rj77oI
09/15/2026
This week kicks off our annual associate fundraising campaign for United Way. This year’s theme: The Magic of Giving, Making Dreams Come True has already inspired many hours of planning and fun so we can support our communities! https://bit.ly/4yxtby2
09/14/2026
Join us at upcoming job fairs!
This week, we’ll be at the UW-Madison Career Fair and the Milwaukee Actuarial Collegiate Conference.
Get all the details by visiting our Events page: https://bit.ly/46aQIc6
09/09/2026
Want an internship where you do more than observe from the sidelines? Meet with Sentry on a campus near you to discuss our hands-on internship opportunities.
Sentry is coming to a campus near you! https://bit.ly/4ifotAd
08/31/2026
As summer comes to a close, we celebrate the hard work, growth, and accomplishments of our interns with a banquet in their honor. Thank you for contributing to Sentry this summer!
Celebrating our 2026 interns: https://bit.ly/4c8vtuY
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1800 North Point Drive
Stevens Point, WI
54481
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