Careers

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.

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.

Corporate Learning is essential to our organization. From facilitating instructor-led training sessions to growing and managing a robust library of interactive learning and organizational development resources, our Corporate Learning teams help associates unleash their talents and thrive in their work systems.

Our Customer Service & Operations team assists our customers across the company. This nimble team works together to assist in questions, claims, and policy changes, with associates located across the U.S.

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.

As part of our hospitality business, Sentry owns and operates SentryWorld, home to the Midwest’s premier parkland golf course and one of the area’s most dynamic event, recreation, lodging, and dining venues.

Our Human Resources teams play a critical role by helping our associates on their professional and personal development journeys. From recruitment and benefits enrollment to employee relations and policy creation, Human Resources ensures associates get the information and support they need to succeed in their roles.

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.

Our internship program is open to students across the country. Our interns gain experience, learn about the insurance industry, and engage in community events.

Our Investments team manages all aspects of our investment discipline and portfolio—from initial strategy, research, and analysis to real-time execution. Team members are essential to Sentry’s overall strength and success, helping the company build a surplus in excess of $8 billion.

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.

We’ve been helping protect our policyholders for more than 120 years. We believe part of that service includes helping prevent losses from happening in the first place. Our proactive, knowledgeable Safety Services team helps our customers create a culture of safety.

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. Our Marketing group is comprised of five teams: Brand Marketing, Corporate Communications, Creative, Customer Research, and Digital Marketing.

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.

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.