Sentry's Operational Support Technician – 401K supports the operational needs by processing and responding to customer inquiries and needs.
What You’ll Do
As an Operations Support Technician – 401K associate you will…
What it Takes
Positions filled in Freeport, IL based on experience and qualifications, the pay range for this position on a hourly basis is $18.41 - 27.64
What You'll Receive
At Sentry, your total rewards go beyond competitive compensation. Below are some benefits and perks that you’ll receive.
About Sentry
We take great pride in making Forbes’ list of America’s Best Midsize Employers. A lot of different factors go into that honor, many of which contribute to your job satisfaction.
Our bright future is built on a long track record of success. We got our start in 1904 and have been helping businesses succeed and protect their futures ever since. Because of the trust placed in us, we’re one of the largest and financially strongest mutual insurance companies in the United States. We’re rated A+ by A.M. Best, the industry's leading rating authority.
Our headquarters is in Stevens Point, Wisconsin, with offices located throughout the United States. From sales to claims, and information technology to marketing, we enjoy a rewarding and challenging work environment with opportunities for ongoing professional development and growth.
Get ready to own your future at Sentry. Opportunities await!
Amelia Sacco
Equal Employment Opportunity
Sentry is an Equal Opportunity Employer. It is our policy that there be no discrimination in employment based on race, color, national origin, religion, sex, disability, age, marital status, or sexual orientation.

In 1904, members of the Wisconsin Retail Hardware Association founded their own insurance company—one built on mutual support, shared strength, and a commitment to service. That legacy remains part of who we are today.
Our continued focus on personal service and Midwestern values helped us earn the trust of businesses across the country. Many of our customers have worked with us for generations.
And we can be there for you.
Our business insurance products are designed to help protect what matters most—your operations and your people. This includes property, casualty, life, and specialty insurance, as well as annuities and retirement.
Whether you’re a small business or a growing operation, we offer industry-specific expertise to help you manage risk with confidence.
Our Stevens Point, Wisconsin, headquarters is the flagship of our business, which is supported by claims offices strategically located throughout the United States. With assets of $27.5 billion and a policyholder surplus of $8 billion, Sentry is rated A+ (superior) by AM Best, the industry’s leading rating authority.*
To learn more about us, the industries we serve, and the products we offer, visit link.sentry.com/Sentry-HomePage.
The content provided here is for informational purposes only: link.sentry.com/Sentry-Disclaimer.
View our underwriting companies at link.sentry.com/Sentry-Disclaimer
*Assets and policyholder surplus are as of December 31, 2024, and represent the aggregate total for all members of the Sentry Insurance Group and are not reflective of any individual underwriting company. Sentry has an AM Best Financial Strength Rating (FSR) of A+ (superior), current as of June 2024. For details about AM Best’s rating scale, see ambest.com/ratings/guide.pdf.