Demo

Customer Service Representative

Sentry
Freeport, IL Full Time
POSTED ON 4/8/2026
AVAILABLE BEFORE 5/7/2026
At Sentry, our priority is providing exceptional customer service and we currently have an opening for you to join this exciting team.

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 coming to us will receive in total a $1000 Sign-on Bonus: $1500 Sign-On Bonus for Bilingual over the course of one year**
  • New Hires coming to us with a Property & Casualty Producers license will receive in total a $1,000 sign-on bonus paid over the course of 6 Months in addition to our new hire sign-on bonus**

As a Member Of Sentry’s Customer Service Team, You Will Be The First Phone Contact With Our Customers. In Addition, You Will

  • Ensures a quality customer experience for our insureds and customers by reducing friction points and ensuring an effortless process. Listens to and assesses customer needs to take appropriate action to fulfill their requests. As a key point of contact for customers, builds positive relationships and creates customer confidence, loyalty and retention by resolving requests using knowledge, empathy and sound judgment. Provides timely customer service meeting or exceeding specified service standards.
  • Receives 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.
  • Navigates multiple systems and technologies to provide and gather information, document actions taken, and accurately resolve service situations in support of insureds and customers.
  • Records and files 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.
  • Researches and identifies contact center problems and issues using standard procedures. May assist with handling issues and communicating updates to peers and management. Escalates more complex issues as needed.
  • Reports trends, issues and feedback learned from customer interactions to support continuous improvement.

What It Takes

In order to be eligible for this elite opportunity you must meet the following criteria:

  • High school diploma
  • Proficiency in Spanish preferred, but not required
  • 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.
  • Ability to meet or exceed attendance requirements, providing reliable and predictable attendance. Hours for this job include nights, weekends, holidays.
  • Possesses basic critical thinking, creativity, and problem-solving skills to provide positive resolution

Positions filled in Freeport, Illinois this position will pay $15.76 - $23.65

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 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 since 2017. 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!

Thank you for your interest in Sentry!

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.

Salary : $16 - $24

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