Sentry Insurance

We’ve been building powerful relationships since 1904
Today, we’ve grown to become a member of one of the largest and most financially secure insurance groups in the country by never forgetting where we came from. Or why. Perhaps that’s why many of our about one million customers have been with us for decades.
If you’re like us, you don’t want to do business with a faceless institution. You want to know what motivates the people who move a business. You want to know who we are, and what we’re all about. We get that, because it’s how we do business too. We work to get to know our customers and their businesses. Why? Because it helps us provide the best possible insurance solutions.
At Sentry—because we are a mutual insurance company—our business is built on a foundation of service to our policyholders. Although we’ve grown and changed a lot over the past 110 years, one thing hasn’t changed. We still work to serve our policyholders, and to help their businesses thrive. Our products and services are made possible by a dedicated team of associates, many of whom have been with us for decades. Over 2,000 associates in Stevens Point, Wisconsin, and another 2,000 around the country, work each day to help our policyholders prepare for the unexpected and plan for the future.
We pride ourselves on providing individualized service to our customers. And one of the ways we do this is by using dedicated teams to serve specific industries. Over the years, departments have grown organically around our products and services.
Careers
Whether you’re new to the job market, looking to advance your career or are a seasoned professional, we offer an array of rewarding career opportunities across a variety of functions, from information technology, claims, sales and underwriting, to marketing, human resources, finance and more.
Our associates are the most important part of our company
We became one of the most financially strong mutual insurance companies in the U.S. by striving to provide the best possible service to our business customers. We do this by having conversations, forming relationships, and getting to know the people we work with and their businesses.
We make that same commitment to our associates. When you join Sentry, we don’t just want you to perform tasks each day. We want you to enjoy your time with us. You’re in the driver’s seat of your career path here—sharing feedback, creating goals, accessing professional development resources, and identifying how you can contribute to both your success and the success of the company. Yes, we work hard. But we work with the purpose of helping others, and with the understanding that there’s more to life than work. We invite you to learn more about us. You’ll find we’re much more than insurance.

Search among Sentry Insurance jobs
| Jobs: 1 - 10 of 74 |
Middle Market Underwriting Specialist
Irvine, California
Applies Underwriting policy, philosophy and procedures to evaluate the acceptability of submitted business. Based on qualifications and experience, this position can be filled at either an Underwriting Specialist or Senior Underwriting Spec...
7h
| Job Type | Full Time |
Madison, Wisconsin
Sentry's HR Specialists serve as the key HR representative in the field office in which they are located. This role will be located at our Middleton, WI office location in a hybrid work model. The HR Specialist provides support and guidance...
7h
| Job Type | Full Time |
Learning Leader - Corporate & Leadership, Professional & Personal Development
Stevens Point, Wisconsin
Lasting, meaningful learning in the workplace doesn't happen by chance - it's intentional. It takes strategy, insight, and leadership to create experiences that help people perform at their best. That's where you come in. As a Learning Lead...
1d
| Job Type | Full Time |
Claims Representative - Commercial Liability
Nashville, Tennessee
Efficiently investigate and resolve insurance claims. You'll manage a caseload, negotiate settlements, and partner with stakeholders to ensure fair, accurate outcomes. This role will be filled in our Stevens Point, WI - Division Street or N...
1d
| Job Type | Full Time |
Claims Representative - Commercial Liability
Stevens Point, Wisconsin
Efficiently investigate and resolve insurance claims. You'll manage a caseload, negotiate settlements, and partner with stakeholders to ensure fair, accurate outcomes. This role will be filled in our Stevens Point, WI - Division Street or N...
1d
| Job Type | Full Time |
Customer Service Representative Translator
Freeport, Illinois
Ensures quality customer service by interpreting phone calls for personal and commercial lines insureds and claimants. Translates and transcribes documents and recordings accurately. What You'll Do As the translator for Sentry Insurance, yo...
1d
| Job Type | Full Time |
Customer Service Representative Translator
El Paso, Texas
Ensures quality customer service by interpreting phone calls for personal and commercial lines insureds and claimants. Translates and transcribes documents and recordings accurately. What You'll Do As the translator for Sentry Insurance, yo...
1d
| Job Type | Full Time |
Customer Service Representative Translator
Goldsboro, North Carolina
Ensures quality customer service by interpreting phone calls for personal and commercial lines insureds and claimants. Translates and transcribes documents and recordings accurately. What You'll Do As the translator for Sentry Insurance, yo...
1d
| Job Type | Full Time |
Customer Service Representative Translator
Stevens Point, Wisconsin
Ensures quality customer service by interpreting phone calls for personal and commercial lines insureds and claimants. Translates and transcribes documents and recordings accurately. What You'll Do As the translator for Sentry Insurance, yo...
1d
| Job Type | Full Time |
Facilities Technician (Entry Level)
Stevens Point, Wisconsin
Responsible for ensuring SentryWorlds property and mechanical equipment is maintained in the best possible condition with the least amount of inconvenience to guests and associates. AtSentryWorld, we're focused on our guest experiences; thi...
2d
| Job Type | Full Time |