Who we are

Our associates are essential to our long-standing stability and success—so we provide resources to help you grow professionally and personally. Learn more about us.

What we offer
At Sentry, your Total Rewards benefits package goes beyond competitive compensation and generous paid time off. We provide benefits that focus on the whole person.
We believe in supporting the communities where we live and work—and providing time for our associates to do the same. Learn about our efforts across the country.
Brands of Sentry
We serve customers across a variety of industries and walks of life. Get to know more about us and our history of protecting others.


Wherever you are in your career journey, you can enjoy an array of rewarding opportunities at Sentry. We offer positions within Customer Support, Claims, Information Technology, Underwriting, Sales Finance, Actuary, Human Resources, Marketing and more—many of which don’t require you to have previous experience in insurance.

Customer Support
Sentry Insurance is dedicated to being there for our customers when they need us most. Our quick-thinking, knowledgeable Customer Service associates are committed to providing outstanding service and support to all of our customers.
Sentry Insurance is rooted in being there for our customers when they need us most. Our quick-thinking, customer-oriented Claims associates are on the front lines delivering on our promise, providing outstanding service and supporting our customers in their time of need.
Information Technology
Sentry Insurance is dedicated to the development of our technology staff and investment in our information systems. Our Information Technology associates play a critical role in our business, developing and maintaining an array of applications and technology across the company.
Underwriting Services
Sentry’s Underwriting associates play a critical role in our core operations, analyzing the risks and exposures of prospective insurance customers to support all of our company’s business segments.
At Sentry Insurance, we make a powerful promise to all of our policyholders—to be there when they need us most. As a Sentry Sales associate, you have the opportunity to sell something more than just a product and be part of something more than just a business.
Finance and Accounting Services
Sentry Insurance is part of one of the largest and most financially secure mutual insurance groups in the U.S. Our Finance team plays a big role in our success and in safeguarding the company’s reputation and fostering trust among stakeholders.
We have a long-standing tradition of actuarial excellence. Our analytically minded, knowledgeable Actuarial associates provide sound, well-supported research, analysis, and recommendations to formulate the pricing across all of our business lines.
Human Resources
Sentry’s Human Resources associates play a critical role throughout our organization, helping all of our associates on their journey from before date of hire on into retirement. From recruitment, onboarding and benefits enrollment to employee relations, development, policy creation, support and everything in between, our HR team helps Sentry associates navigate the abundance of information available at their fingertips.
Sentry’s first-class corporate Marketing department works to manage and raise the profile of Sentry’s brands through the creation and execution of innovative, effective marketing plans and tactics for all of our business segments. Our Marketing group is comprised of five teams: Brand Marketing, Corporate Communications and Content, Creative, Customer Research and Digital Marketing.
At Sentry, integrity and trust are the driving principles in how we do business. Our Legal department helps position Sentry as a responsible leader in the insurance marketplace. Explore the numerous roles available in our Legal department that range from insurance and employment law to litigation management.
Loss Control
Sentry Insurance has been protecting our policyholders for more than 100 years, and our protection spans beyond insurance alone. Our proactive, knowledgeable Safety Services associates help our customers save lives, time and money.
Sentry’s leading-edge Investments team works tirelessly to manage all aspects of our investment discipline and portfolio—from initial strategy, research and analysis to real-time execution. Our Investments group is essential to Sentry’s overall strength and success, both short and long-term.
Hospitality and Recreation
We truly are more than insurance. Sentry Insurance also owns and operates SentryWorld, the Midwest’s premier parkland golf experience and one of the area’s most dynamic event, recreation and dining venues. Sentry’s home office is also home to @1800, featuring fine dining as well as a stylish lounge, gallery and theater.
Our internship program focuses on gaining experience, learning about the insurance industry, and engaging in community events.
Corporate Learning
Sentry’s Corporate Learning associates are essential to our organization, helping our associates unleash their individual talents and thrive in their work systems. From facilitating instructor-led training sessions to growing and managing a robust library of interactive learning and organizational development resources, our Corporate Learning team helps Sentry associates realize their goals and take their careers to the next level.

Our locations

At Sentry, we’re proud to call Stevens Point, Wisconsin, our home. But we have roots nationwide. We’re proud to have many field offices located throughout the U.S. The communities in which we live and work embrace cultural diversity, offer safe neighborhoods, provide quality education, and boast a variety of entertainment, lifestyle, and recreational activities.

Stevens Point, WI
At Sentry Insurance, we are proud to call Stevens Point, Wisconsin our home. With its convenient central location, breathtaking natural landscape and host of modern amenities, the Stevens Point area is a wonderful place to live, work and play.
Charlotte, NC
As one of the fastest growing cities in the U.S., Charlotte is an ideal home for our southeast regional business operations. Our office is located in a beautiful development just minutes from downtown.
Davenport, IA
Located in the heart of the Quad Cities near the Mississippi River, our Davenport office is an engaging environment where our associates collaborate, encourage, and support each other.
Edwardsville, IL
Residing on a beautiful campus reflecting the horticultural industry it serves, our Edwardsville office is home to our Hortica® brand. Nearly 100 associates work here, creating a close-knit, collaborative environment.
El Paso, TX
El Paso, Texas Our El Paso field office enhances our presence in the Southwest and positions us to better serve and grow our customer base in that area. El Paso has a growing and diversified economy that’s both business and family friendly, and we’re looking to offer a wide variety of positions in this location.
Freeport, IL
Our Freeport office is built around a culture of support, encouragement, and recognition. This leads to a positive work environment where we focus on teamwork and celebrate success.
Goldsboro, NC
Our Goldsboro office is one of our main customer services hubs. In Goldsboro, our associates create a family atmosphere through collaboration, support, and encouragement.
Irvine, CA
We couldn’t ask for a better location for our Pacific regional office. Our associates enjoy a beautiful setting and numerous amenities inside and outside the office.
Madison, WI
As Wisconsin’s capital and second largest city, Madison combines abundant natural beauty, friendly communities, great schools, diverse cultural opportunities and a host of modern amenities.
Richmond, VA
Virginia’s state capital and fourth largest city, Richmond combines rich history, abundant natural beauty, friendly communities, great schools, endless entertainment opportunities and a host of modern amenities.
Scottsdale, AZ
Affectionately dubbed “The West’s Most Western Town,” Scottsdale combines abundant natural beauty, friendly communities, great schools, diverse cultural opportunities and a host of modern amenities.
Westford, MA
Westford is steeped in history and combines abundant natural beauty, friendly communities, great schools, a variety of recreational and entertainment opportunities and a host of modern amenities.
Windsor, CT
This office is located in a quaint town center not far from the state capitol, making it an ideal spot for one of our Northeast regional hubs. Our associates enjoy a fun, vibrant environment with modern amenities.

College students

Our paid internship or co-op program opportunities provide you with practical experience in real-world, real-work situations. You’ll receive the support you need, learn new skills, and work with the latest technology. Plus, we’ll have a lot of fun along the way. Check out our programs.

Our internship program focuses on gaining experience, learning about the insurance industry, and engaging in community events.
Intern blog
What better way to learn about an internship at Sentry than from those who have participated in our program? Watch these videos.
IT and IS co-op programs
Join a select group of college students who get to make a real impact while working in a modern, collaborative space designed exclusively for co-op participants.