Customer Service Representative
Confirmed on the employer's own hiring board on Oct 1, 2026. First seen by Alion on Sep 29, 2026.
What You'll Do
Take the customer service skills you have acquired over the years to the next level or make a change and start down your new career path today with our growing team of Service Professionals at one of the largest mutual insurance companies in the U.S.!
**New hires receive a $1,000.00 sign on bonus over the course of their first year, with bilingual new hires receiving a total of $1,500.00**
**New hires with a Property & Casualty Producers License receive an additional $1,000.00 sign on bonus, paid over 5 months, on top of our standard new hire bonus**
As a member of Sentry’s Customer Service Team, you will be the first phone contact with our customers. In addition, you will:
- Ensure a quality customer experience for our insureds and customers by reducing friction points and ensuring an effortless process. Listen to and assesses customer needs to take appropriate action to fulfill their requests. Build positive relationships and create customer confidence, loyalty and retention by resolving requests using knowledge, empathy and sound judgment. Provide timely customer service meeting or exceeding specified service standards.
- Receive a high volume of telephone calls for assigned line of business and provides upfront assistance to our insureds and customers in need of service. These needs may include locating, providing or obtaining information or documentation, instructions on how to proceed with a claim, answering questions, routing or transferring calls as appropriate, entering data to begin a claim, etc.
- Navigate multiple systems and technologies to provide and gather information, document actions taken, and accurately resolve service situations in support of insureds and customers.
- Record and file provided information from each call and/or electronic request in the appropriate system application. This may include loss information, received documentation, payment processing, policy changes with customers, etc.
What It Takes
- High school diploma.
- Ability to meet or exceed attendance requirements, providing reliable and predictable attendance. Hours for this job include nights, weekends, holidays.
- Good human relations skills to deal effectively with customer issues in a professional manner.
- Ability to communicate effectively and accurately verbally and in writing.
- Knowledge of how to use a computer, keyboard skills and familiarity with software applications such as Excel and Word.
- Ability to navigate through various technology software to research and accurately resolve service situations is critical to the success of this position.
- Possess basic critical thinking, creativity, and problem-solving skills to provide positive resolution.
- Proficiency in Spanish preferred but not required.
Positions filled in Freeport, Illinois this position will pay $15.76 - $23.65
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.
- Hybrid Flexibility: Enjoy the best of both worlds. With optional work from home on Mondays and Fridays and join your team in the office Tuesday through Thursday to collaborate and learn. We provide the technology and tools you need for both your office and home workspace from day one.
- Dining on Us: Depending on your location, we may provide a stipend that can be used at our on-site cafeteria or a meal allowance to keep you fueled.
- Continuous Learning: Unlock your potential through Sentry University and take advantage of our tuition reimbursement program.
- Comprehensive Benefits: We support your whole self with group medical, dental, and vision insurance along with parental leave, pet insurance, caregiver leave, and wellness resources. Options for HSA, FSA, and Dependent Care FSA are available.
- Work-Life Balance: Enjoy your generous Paid Time Off allowance to rest and take advantage of paid Volunteer Time Off to support your community.
- Investing in Your Future: We’re committed to your long-term financial well-being. We offer a 100% company match on the first 8% you contribute to your 401(k) each pay period, and those funds vest immediately.
- Giving Back: Through the Sentry Foundation, we’re proud to support the United Way and make a difference in our communities.
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!
Erin Haddaway
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.