Sentry Careers

06/22/2026

Summer brings the best of our campuses. From thoughtfully designed indoor workspaces to outdoor areas that invite a break or conversation, our office locations provide a great environment to connect with others and foster collaboration.

06/19/2026

Peyton has brought great enthusiasm and drive during his time as youth apprentice. We look forward to continue watching him develop professionally and personally in our co-op program.

YOUTH APPRENTICE OF THE WEEK:
Peyton Feist is a software engineer youth apprentice at Sentry. He programs software and enjoys coming up with creative solutions along side his team. Peyton would encourage others to try an apprenticeship, as he says "it has only been a positive" on his academic journey.
Peyton's CTE coursework includes AP Computer Science, Cybersecurity (dual enrollment), Accounting 1 and Accounting 2 (dual enrollment), and Intro to Marketing (dual enrollment). He has utilized the Early College Credit Program (ECCP) through UWSP and has taken CIS 120 and 210, along with AI 230. He will be attending UWSP this fall and will continue working with the Sentry Co-op Program. The future is bright for this SPASH Youth Apprentice!

Fact: CTE elective courses and Youth Apprenticeship help create vision in academic and career planning.

06/18/2026

We appreciate our interns and the energy and skills they bring to our company. That’s why we welcome them back for a second internship if they choose. Jake, one of our second-year interns, said the prioritization of our internship program is one of the main reasons he’s back.

College students can gain valuable experience through career development opportunities at Sentry, including internships and part-time co-op roles.

06/16/2026

Welcome back! We’re happy to have Jake (based in Stevens Point, Wisconsin) and Denisse (based in El Paso, Texas) back with us for a second internship. We look forward to your continued insight, growth, and contributions this summer.

Learn more about the student opportunities at Sentry®.

College students can gain valuable experience through career development opportunities at Sentry, including internships and part-time co-op roles.

06/10/2026

Our employees are our greatest assets. At Sentry, we believe in offering benefits, resources, and opportunities to support our employees in all aspects of their lives.

Explore the benefits available to you and apply today! https://bit.ly/3PIE5Av

06/06/2026

Education is one of the core giving areas for the Sentry Insurance Foundation. We invest in both students and the institutions that help shape their careers.

Strategic giving to help build a brighter future: https://bit.ly/4frEGAR

06/03/2026

It was our pleasure to host and engage with these insightful students. Thank you for the great conversations. We hope to see some of you again for actual interviews regarding employment opportunities in the years ahead.

On Friday, Sentry hosted Mr. Greco's World of Business class for their end-of-semester mock interviews. We extend our sincere gratitude to Sentry and our wonderful community business volunteers for donating their time to support our students. Dressed to impress and prepared with resumes, smiles, and firm handshakes, these students truly understood the assignment.

06/02/2026

When Sentry® acquired The General® in 2025, it brought together two companies that value relationships and putting people first.

Learn more about us and explore our career opportunities in Nashville: https://link.sentry.com/sentrycareers

05/29/2026

We’re excited to welcome our 2026 summer interns to Sentry®. More than 30 talented students from across the country are joining us in IT, Claims, Customer Service, Marketing, and more. We’re glad you’re here!

Please welcome our summer interns: https://link.sentry.com/studentopportunities

05/27/2026

We appreciate the skills, energy, and intellect Lukasz and all of the Youth Apprenticeship students bring to Sentry®. We look forward to your continued professional and personal growth.

YOUTH APPRENTICE OF THE WEEK:
Lukasz Dobbs is a Temporary Service Assistant Apprentice at Sentry. "I work with a team. I help code full stack, as well as help with testing, and documentation. I get to participate in team meetings, and give demos on what I've worked on. I am currently writing an automated testing suite to help with regression testing and to take some of the work off of other team members hands." The part of the job he enjoys most are the times he gets to hang out and just talk, like during lunches or engagement events,. He also likes writing code. "I've always enjoyed making and building things, and code is the medium in which I get to use that passion."

Lukasz has completed AP Computer Science and Early College Credit Program (ECCP) UWSP CIS 120, 210, and 230 courses. If you are interested in applying for Youth Apprenticeship, Lukasz said to do it! "It's incredibly enjoyable and you get to meet new people. It's a great entry level job for our age, and you gain valuable work experience."
Lukasz will continue his studies at UWSP this fall while continuing to work with IT in the Sentry Co-op. The future is bright for this SPASH Youth Apprentice!

🎓Congratulations to our graduating SENIOR YOUTH APPRENTICES. We are proud of you all. 🎓

Fact: CTE elective courses and Youth Apprenticeship help create vision in academic and career planning.