Ranked 13th among Wisconsin’s largest private companies by revenue and impact by Deloitte.
This associate will utilize multiple systems to monitor and resolve service-related items that arise to assist with timely completion of service items, annual non-discrimination testing, and other compliance related items. Works closely with 401(k) colleagues for continued education and development of 401(k) technical knowledge.
What You'll Do
As an Associate Client Services Specialist, you will:
Monitor and maintain workflow tasks for assigned clients to ensure requests and services are completed within the required deadlines
Monitor incoming email and voice messages while corresponding with clients to provide accurate information regarding employer contributions, payroll, and plan information
Collect, verify, and update required customer information accurately within Sentry systems
Develop and maintain an understanding of Sentry’s plan documents, contracts, systems, and compliance requirements
Perform other job-related duties as assigned
What it Takes
Associate degree or equivalent work experience
0-2 years of related work experience
Prior retirement or 401(k) experience and knowledge is desired
Strong verbal and written communication skills
Successful completion of educational courses, such as CEBS or ASPPA, are beneficial
Computer skills, math aptitude, and ability to communicate and provide exceptional service to our customers required
Ability to prioritize workload and handle several projects simultaneously
Ability to analyze contracts and documents is required
Positions filled in Freeport, Illinois this position will pay $21.44 - $32.21
Positions filled in Denver, Colorado this position will pay $23.60 - $35.43
Here is what you can look forward to as part of our team:
At Sentry, your total rewards go beyond competitive compensation. We’re committed to supporting the whole you, which is why we offer a comprehensive package designed to help you thrive both professionally and personally.
Why Join Sentry?
At Sentry, we believe our people are the heart of our success. We’re proud to be recognized for the culture we’ve built, earning spots on Forbes’ lists for America’s Best Midsize Employers and Best Employers for New Grads, as well as Newsweek’s America’s Greatest Workplaces for Women and Diversity. These honors reflect our commitment to your professional satisfaction and growth.
Building on a Legacy
Our future is bright, but it’s anchored in a long history of stability. Since our founding in 1904, we’ve dedicated ourselves to helping businesses protect their futures. That trust has made us one of the largest and most financially stable mutual insurance companies in the U.S. We’re proud to have maintained an A+ rating from A.M. Best, the industry’s leading authority, for over 30 years.
Your Career, Our Community
Whether you’re working at our headquarters in Stevens Point, Wisconsin, or one of our many offices across the country, you’ll find a challenging and rewarding environment. Explore the Our Teams tab on our Career Page to see the diverse career paths we offer, with a focus on ongoing development and professional growth.
Ready to own your future? Join us 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.
Our commitment to creating a positive, people-first culture hasn’t gone unnoticed. We’re proud to be recognized for our outstanding workplace culture.

Ranked 13th among Wisconsin’s largest private companies by revenue and impact by Deloitte.
Sentry is one of America’s Best Midsize Employers, according to Forbes.