Sentry Careers

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.

05/22/2026

Our SentryWorld campus attracts visitors from across the country to enjoy world-class dining, lodging, and golf.

You can help create a memorable experience for these guests. We offer generous paid time off, an 8% 401(k) match, and perks such as discounted meals and golf rates.

Great benefits in a beautiful setting: https://bit.ly/4eWpFXC

05/20/2026

Your privacy matters to us.

We care about your privacy and security. During our hiring process, we don’t request personal or banking information via social media or text messaging applications. Please contact us at [email protected] if you have any questions.

Explore our current openings. https://link.sentry.com/sentrycareers

05/18/2026

Whether you’re starting your career at Sentry® or taking your next step elsewhere, congratulations to the Class of 2026.

A special welcome to our former interns and co-op students who are joining us full-time. We’re glad to have you on the team.

Congratulations to the Class of 2026: https://link.sentry.com/sentrycareers

05/15/2026

We recently welcomed local high school students to our home office for a day focused on learning, leadership, and career growth. Students participated in sessions designed to strengthen leadership and interview skills while also getting a closer look at financial planning and life at Sentry®. Thanks for spending the day with us!

05/13/2026

Good luck on finals!

Finals week is here—you’ve got this. Along with studying, focus on how you manage your time and energy. A plan, regular breaks, and asking for help when needed is a recipe for success. https://link.sentry.com/sentrycareers

05/06/2026

We believe in continually investing in our employees’ experience and reaffirming our commitment to the communities we’re located in. Get a preview of the sweeping renovation project taking place at our headquarters in Stevens Point, Wisconsin by visiting the link below.

The largest facilities project in our 120-year history: https://www.sentry.com/about-us/annual-report

05/04/2026

We appreciate the enthusiasm and skills Lorena brings to Sentry. As with all of our youth apprentice students, Lorena performs applicable work we implement in our systems. Thank you for all your hard work and dedication.

YOUTH APPRENTICE OF THE WEEK:

Lorena Hill is a second year software engineer youth apprentice at Sentry. She works in the auto-assignment process area. Lorena writes, tests, and deploys code to improve the efficiency and duration of how claim representatives are assigned to claims. She communicates between teams to figure out what the business needs and then analyzes the effects of any changes made. Her favorite part of the job is hearing about the real-world applications and implications of the work she does.
Lorena would recommend taking a youth apprenticeship, as "it is a great way to step out of your comfort zone, and figure out if you're interested in applying what you've learned at a job with real applications."
Lorena's CTE coursework includes AP Computer Science and Independent Study Python. She enrolled in UWSP (Early College Credit Program) CIS 120.
Lorena will be attending Augustana University where she will be double majoring in Data Analytics and Engineering Physics. She will also be competing in Track and Field. The future is bright for this SPASH Youth Apprentice!

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

04/30/2026

We’re proud to offer a Youth Apprenticeship program for high school students across a variety of disciplines. It’s a great opportunity to explore career options, gain professional experience, and learn new skills. We appreciate all of our participants enthusiasm and insight as this program continues to grow. https://link.sentry.com/careersatsentry