Careers
Company culture
Bringing together people, purpose, and passion
If you're curious about what it’s like to work at Sentry, you'll find that our culture goes beyond the job. It’s about belonging to a team that values growth, supports one another, and serves our communities.
The way we work together
Collaboration is at the heart of the Sentry workplace environment. We value different perspectives and encourage team members to bring their authentic selves to work—because the best ideas come from those who feel heard, supported, and empowered.
When Sentry has fun
Work isn’t just about the bottom line—it’s also about enjoying the journey. From team-building outings to themed office events, these moments of community reinforce what makes working at Sentry special. They help build stronger teams, boost morale, and remind us all that it's possible to do meaningful work while having fun along the way.
A culture of learning and support
We believe the best investment we can make is in our people. That’s why Sentry is committed to continuous learning and professional growth. Whether it’s through internship programs, professional skill development, or leadership development opportunities, these investments not only strengthen how we work together, but they also shape how we show up for our customers and communities.
Committed to community
We’re proud to support causes that matter—to our team, our customers, and the places we call home. It's a core part of the Sentry company culture and a reflection of the Sentry Insurance values that guide everything we do.
Volunteer time off
Our Total Rewards benefits package includes volunteer time off (VTO). The goal is to support volunteer activities that lift up our communities.
Matching gift program
Make a bigger impact in your community. We’ll match your donations, dollar for dollar up to specified limits, to eligible organizations.
Supporting students
We believe in the power of education and the value it brings to our communities. That’s why we sponsor scholarship programs for dependents of Sentry associates.
The Sentry Insurance Foundation
At Sentry, giving back is who we are. Through the Sentry Insurance Foundation, we invest in education, workforce development, and our local communities. Our philanthropic efforts are grounded in our belief in creating strong relationships, just like the way we do business.
237
Scholarships
awarded annually.
$1.7M
Raised
for United Way in 2024.
85
Organizations
supported each year.
My Sentry experience
When I come to work, I’m really excited about programming with my friends—that’s what it feels like.
My Sentry experience
We come together and make more than the sum of our parts, and that’s very exciting for me.
My Sentry experience
Elise Buzzell
Associate Software Developer
Michigan
The culture at Sentry is very community-driven, with a strong focus on collaboration and shared success. I’ve received a great deal of support regarding my future growth and goals.
My Sentry experience
The team culture is my favorite thing about Sentry…the people surrounding you make it enjoyable every step of the way.
My Sentry experience
Sentry has really invested in me, and I take a lot of pride in that.
My Sentry experience
Andrea Loscher
Associate Claims Representative
Stevens Point, WI
The team culture at Sentry is extremely supportive. It’s such a great feeling to be a part of a team that looks out for each other and always has your best intentions and success in mind.
My Sentry experience
It’s just such a great place to work and to be.