Careers
Our teams
Explore the departments that make up Sentry. Insurance is the foundation of what we do, but there’s so much more to our organization. Keep scrolling to discover where you’ll fit best.
All locations
All locations
Own your future with Sentry Insurance
Whether you’re new to the job market, looking to advance your career, or are an experienced professional, we offer rewarding career opportunities across a variety of fields in the insurance industry—and, through our SentryWorld® brand, the world of hospitality.
Regardless of your role, you’ll have access to learning and development resources that will help you succeed in your current position and prepare for future opportunities. We encourage every associate to take charge of their career growth through participating in formal training, on-the-job projects, and ongoing professional development conversations with leadership.
Sentry teams
These dynamic, innovative teams support—and, in many cases, work directly with—our insurance customers.
Actuary
Our analytically minded, knowledgeable Actuarial associates provide sound, well-supported research, analysis, and recommendations to formulate the pricing across all of our business lines.
Claims
Our customer-oriented Claims associates are key to delivering on our promise, providing outstanding service and supporting our customers in their time of need.
Customer Service
Our Customer Service team offers friendly, knowledgeable support for customer questions, claims, and policy changes. With associates nationwide, they work together to be there for our customers.
Data Analytics
Through strategic collaboration, sophisticated tools, and ongoing education, our Data Analytics team provides Sentry with a competitive advantage by supporting data-driven innovation and efficiency.
Finance, Accounting, and Investments
Our Finance, Accounting, and Investment teams are key to our success, safeguarding our reputation and fostering stakeholder trust by overseeing financial reporting, taxation, and auditing.
Human Resources
The Human Resources team—including Corporate Learning—support our associates on their professional and personal journeys, from recruitment and benefits enrollment to interactive education.
Information Security
Our Information Security team helps protect both Sentry and our customers by keeping sensitive and confidential information safe, proactively identifying solutions and responding to security threats.
Information Technology
Our Information Technology (IT) associates play a critical role in our business, developing and maintaining an array of applications and technology across the company.
Legal
This team helps position Sentry as a responsible leader in the insurance marketplace, with roles ranging from insurance and employment law to litigation management.
Marketing
Our corporate Marketing department manages and raises the profiles of Sentry’s brands through the creation and execution of innovative, effective marketing plans and strategies.
Product Development and Management
This collaborative, data-driven team develops, analyzes, and implements insurance products for our personal lines brands, Dairyland® and The General®.
Risk Control
Our proactive, knowledgeable Safety Services team members help our customers create and maintain a culture of safety—to help stop losses from happening in the first place.
Sales
Our Sales associates get to know our customers to help them protect their assets, employees, and longevity. They provide the specialized expertise our insureds expect and deserve.
Underwriting
Our Underwriting associates are critical to our core operations, analyzing the risks and exposures of prospective insurance customers to support our company’s business segments.
Additional teams
We have several specialized teams that are unique to Sentry. We encourage you to explore our open job listings to learn more and see if these roles may be a good fit for you.
SentryWorld teams
We also own and operate SentryWorld, the Midwest’s premier parkland golf experience and one of the area’s most dynamic event, recreation, lodging, and dining venues.
Event management
SentryWorld is among Wisconsin’s most popular event destinations, with versatile spaces for weddings, conferences, and more. Our team handles the logistics so our guests can focus on enjoying their visit.
Golf
Keeping our 18-hole championship golf course operating at peak performance requires contributions from a range of teams, including groundskeepers, Pro Shop employees, and licensed PGA instructors.
Lodging
The Inn at SentryWorld is our boutique hotel, with golf course views and a range of amenities. From maintenance staff to front desk attendees, we offer full-time, part-time, and seasonal positions.
Recreation
Golf isn’t SentryWorld’s only onsite sport! Guests can enjoy tennis, pickleball, volleyball, and other indoor activities—with SentryWorld staff on hand to assist, coordinate equipment rentals, and more.
Restaurants
SentryWorld is home to three restaurants—Muse at Sentry, PJ’s – SentryWorld, and the Library Café—each with its own unique atmosphere and menu options, but with a shared commitment to local flavors.