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.

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.

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.

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.

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, 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 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.

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

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.

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.

Our Mountain Region office opened in 2023. This office currently serves agents in Colorado, Arizona, and Utah. It’s located minutes from Denver’s downtown district in Greenwood Village.

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.

Our El Paso field office enhances our presence in the Southwest and positions us to better serve our growing customer base in the area. Our El Paso location is one of our fastest-growing offices, offering a variety of customer service-related positions.

Our Freeport office is built around a culture of support, encouragement, and recognition and is home to associates working in Customer Service & Operations, IT, and Personal Lines.

Our Goldsboro office is one of our main customer services hubs. In Goldsboro, our associates have created an engaged family atmosphere where supporting their local communities is a passion.

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.

Just 90 minutes from our headquarters, our Madison offices (four in all) serve as home for our Government & Regulatory Affairs, Personal Lines, Co-Op, and Midwest Region associates, among others.

Milwaukee serves as one of the homes for our Midwest Region. This close-knit office is located halfway between the Mayfair Mall and the Milwaukee County Zoo.

Portland is home to our growing Northwest Region, serving the three surrounding states. Staff consists of underwriters, customer support, and 401(k) specialists.

Our Richmond field office primary houses Claims associates. Associates here work closely together and are highly engaged in company and community events.

Scottsdale combines abundant natural beauty, friendly communities, great schools, diverse cultural opportunities and a host of modern amenities.

Westford serves as our Northeast field office, consisting of primarily Claims associates, who serve our customers across the country.

Our Northwest Region office is located in a quaint town center not far from the state capitol. This tight-knit office serves six surrounding states.