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 rat
08/11/2026
When students have the tools they need to explore new technologies and step into the modern workforce, our whole community benefits. Let’s continue learning and growing together.
Sentry is empowering the future of learning for our students! 🚀🤖
We are beyond grateful to Sentry for their incredible $1.5 million grant supporting technology innovation across local schools through 2028!
Thanks to this generous investment, we’re launching an initiative that will bring a state-of-the-art AI Innovation Lab to SPASH. It will feature industry-standard tools in artificial intelligence, cybersecurity, data analytics, and digital design. 💻📊
Through partnerships with UW-Stevens Point and Mid-State Technical College, our students will also gain hands-on, real-world skills to thrive in an evolving workforce.
Thank you, Sentry, for investing in our community's schools!
08/04/2026
Hands-on experience is a vital part of learning and growth, and Sentry is proud to work with dedicated students like Elizabeth though the Youth Apprenticeship program at SPASH. Keep up the good work!
YOUTH APPRENTICE OF THE WEEK:
Elizabeth Fish is an IT youth apprentice at Sentry. She is a member of the infrastructure delivery team and IOC. Her favorite part of the job is working in a corporate environment and working on a team. "I love getting real world job experience in a business and having a team that I can ask for help."
Elizabeth's CTE coursework includes Online Cybersecurity and AP Computer Science. Advice for future Youth Apprentices: It's a great way to get a head start in a career path to see if that's what you really want to pursue. The future is bright for this SPASH Youth Apprentice!
Fact: CTE elective courses and Youth Apprenticeship help create vision in academic and career planning.
07/31/2026
Our interns are valuable employees here at Sentry. And our culture is to assist and guide them during their time with us. What I enjoy about my Sentry® internship:
Internships for College Students | Sentry Insurance Careers Explore Sentry's paid internships across various departments. Gain real-world experience, competitive pay, and potential career advancement.
07/29/2026
At Sentry®, every intern is paired with a mentor who provides the guidance, tools, and support they need as they work on meaningful projects that make an impact.
Discover the other benefits our interns enjoy.
Internships for College Students | Sentry Insurance Careers Explore Sentry's paid internships across various departments. Gain real-world experience, competitive pay, and potential career advancement.
“This internship exceeded my expectations”
Through our internship program, we want students to gain first-hand experience working in a professional environment. Hear from Taylor about the skills he gained as an intern at Sentry®. https://bit.ly/3TYYumj
The renovation of our headquarters in Stevens Point, Wisconsin, will create a more modern, collaborative workplace, while reinforcing our long-term commitment to the community we’ve called home for more than 120 years.
Investing in our employees and hometown: https://bit.ly/4utPKl5
Our summer internship program is underway, and our interns are making an impact. Through hands-on experience and opportunities to connect with each other and the community, they’re building skills for the future.
Interested in joining us? Explore our internship opportunities. https://bit.ly/4vtI5Dz
We offer multiple career paths—and the opportunity to find one that fits you. At Sentry®, we believe in providing opportunities for advancement—and exploring different career paths. Hear about the career journey one of our employees has taken during his time with us.
Explore our current openings and apply today: https://bit.ly/4fuh4Lr
07/08/2026
Every intern at Sentry® has a mentor who guides them, offers advice, and helps ensure a meaningful experience that propels their career aspirations.
Discover the other benefits our interns enjoy.
Mentors our interns can count on Explore Sentry's paid internships across various departments. Gain real-world experience, competitive pay, and potential career advancement.
07/04/2026
Happy Fourth of July from all of us at Sentry®. We hope you have an enjoyable and safe holiday.
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1800 North Point Drive
Stevens Point, WI
54481