Supervises a direct reporting staff who provides customer service to a variety of clients.
What You’ll Do
The ideal Customer Service Supervisor have effect leadership skills and is able to provide direction and motivation to their staff to ensure Sentry continues to provide exceptional customer service. You’ll do this by:
Developing and implementing customer service standards
Coaching, counseling, and motivating your customer service team
Improving customer service quality results by studying, evaluating and formulating ideas
Maintaining knowledge of new or revised telecommunications systems
Providing work direction to your staff
Implementing policies and procedures
Providing expertise in handling sensitive/unusual customer service issues
Scheduling staff accordingly and tracking performance
Assisting with budget preparation and controlling operating expenses
For positions filled in Freeport Illinois this position will pay a salary of $61,900-$92,900.
What it Takes
Bachelor's Degree or equivalent work experience
Proficiency in Spanish preferred, but not required
5 years of previous work experience or knowledge of a customer service environment and previous supervisory experience
Ability to provide leadership to employees within a fast-paced call center environment
Ability to prioritize work and maintain appropriate service standards
Ability to analyze data, identify trends, and communicate results
Working knowledge of telecommunication systems and call center software
Knowledge of insurance processes, procedures, and systems beneficial
Ability to respond to sensitive inquiries or complaints from customers, state insurance departments, producers, and others with tact and diplomacy
Must be available to work non-standard hours including nights, weekends and holidays as needed.
What You'll Receive
At Sentry, your total rewards go beyond competitive compensation. Below are some benefits and perks that you’ll receive.
Sentry is happy to offer flexibility through a scheduled Hybrid work model. Monday and Friday work from home if you choose to, Tuesday through Thursday you’ll work in office.
As a Sentry associate, you will have an in-office workspace and materials for your home office. In addition to the laptop, you will receive prior to your start, Sentry will provide equipment for your home office.
Meal Subsidy available for associates who report to an office.
401(K) plan with a dollar-for-dollar match on your first eight percent, plus immediate vesting to help strengthen your financial future.
Continue your education and career development through Sentry University (SentryU) and utilize our Tuition Reimbursement program
Generous Paid-Time Off plan for you to enjoy time out of the office as well as Volunteer-Time off
Group Medical, Dental, Vision, Life insurance, Parental leave, and our Health and Wellness benefits to encourage a healthy lifestyle.
Well-being and Employee Assistance programs
Sentry Foundation gift matching program to encourage charitable giving.
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!
Erin Haddaway
Erin.Haddaway@Sentry.com
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.