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Careers
Working at Sentry
We know our people are the most important part of our organization. Working here means joining a company where we value our employees’ growth, purpose, and personal success.
All locations
All locations
The culture at Sentry Insurance
Life at Sentry is about more than just work—it’s about belonging to a community where your contributions matter, your development is supported, and your well-being is a shared priority.
Our workplace culture is shaped by our values—relationships, conversation, and community. From our day-to-day interactions to the way we support each other’s goals, the employee experience at Sentry is collaborative, engaging, and rooted in a shared commitment to helping others.
Get more with Sentry benefits
In addition to offering flexible essential benefits like medical, dental, vision, and life insurance, we provide benefits that focus on the whole person.
Investing in your future
We’re invested in your long-term success. Enjoy an 8% 401(k) match with immediate vesting, tuition reimbursement, and scholarships for dependents.
Supporting your health and wellness
We support your well-being through on-site wellness centers or gym membership reimbursement and resources that provide help with mental health, caregiving, and finances.
Growing with Sentry
SentryU, our learning and development team, will help you gain new skills, deepen your expertise, and stay sharp in a changing world.
Sentry’s Hiring Process
We want you to feel confident every step of the way. Here’s what to expect:
Let’s talk
If it’s a match, you’ll hear from a recruiter to schedule an interview where you’ll meet with hiring managers.
Decision time
We’ll reach out to the selected candidate with an offer and the next steps for joining the team.
Where is Sentry located?
We’re based in Stevens Point, Wisconsin—with roots nationwide. With regional offices across the U.S., we’re located in communities offer safe neighborhoods, provide quality education, and boast a variety of entertainment, lifestyle, and recreational activities.
A community-minded culture
At Sentry, we believe contributing time, effort, and resources to our communities—and supporting associates in their individual efforts to do the same—is an essential part of who we are. Together, we make an impact.
Matching gift program
We match associate donations and retiree gifts to eligible organizations on a dollar-for-dollar basis, from $25–$7,500 per associate per year.
United Way campaign
Each year, we raise over $1 million for this non-profit organization, supporting communities where our associates live and work.
An award-winning workplace
Our commitment to creating a positive, people-first culture hasn’t gone unnoticed. We’re proud to be recognized for our outstanding workplace culture.
Sentry earned an A+ rating for the 34th consecutive year.
Recognized as one of America’s Greatest Workplaces for Diversity by Newsweek.
Ranked 13th among Wisconsin’s largest private companies by revenue and impact by Deloitte.
Sentry is one of America’s Best Midsize Employers, according to Forbes.
For the second year in a row, Newsweek named Sentry one of America’s Greatest Workplaces for Women.
Forbes names Sentry as one of the Best Employers for new Grads.
My Sentry experience
I actually take pride in working at Sentry.
My Sentry experience
My favorite perk…would have to be the gym. We have a full basketball court, weight room, pool and racquetball room in the basement of an insurance company.
My Sentry experience
Knatali Jaramillo
Senior Customer Service Representative
Goldsboro, NC
My favorite part of the work I do is assisting our callers during a stressful time and giving them the best customer service possible.
My Sentry experience
In terms of professional development, they’re extremely supportive of obtaining certification and other continuing education credits.
My Sentry experience
AJ Bardales
Claims Manager
El Paso, TX
Thanks to Sentry, I’ve earned nine professional designations. Designations support our professional growth, and it’s very encouraging to not worry about the cost of continued learning.
My Sentry experience
We want to have trust in people. We want people to know there is opportunity ahead of them.
My Sentry experience
Sentry is very, very good at getting the things you need to do your job proper.