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This position has closed. Sentry Insurance removed this listing from their careers page on Oct 6, 2026. The interview prep below is still useful, and there are similar open roles at the bottom of this page.

Contact Center Representative - Claims Intake

Sentry Insurance · Freeport, IL · $15.76–$23.65 an hour · Full time

Posted Sep 29, 2026 · We last checked this listing on Oct 4, 2026

Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a time you had to type or enter information while talking with someone.

What they are checking: Their ability to multitask on calls, which first notice of loss work demands.

The posting stresses reliable and predictable attendance. How have you shown that in past jobs?

What they are checking: Their reliability, since phone coverage depends on everyone showing up as scheduled.

Do you speak any languages besides English, and have you used them with customers?

What they are checking: Whether they can serve bilingual callers, which the posting specifically rewards.

How do you stay positive and focused through a long day of back-to-back calls?

What they are checking: Their stamina and mindset for steady, high-volume phone work.

What would you do

You are the first person someone talks to after an accident. How would you start that call?

What they are checking: Whether they can calm and reassure a caller while starting to collect the facts.

A caller is yelling and blaming you for a problem you did not cause. What do you do?

What they are checking: Whether they stay calm and helpful instead of taking it personally.

The team works to meet phone performance goals. How do you balance speed with getting the details right?

What they are checking: Whether they understand that both call times and accuracy matter in a contact center.

A caller asks if their claim will be covered. How do you answer when that is not your decision?

What they are checking: Whether they avoid making promises about coverage while still helping the caller.

About the work

What information do you think you would need to take a first report of a car accident claim?

What they are checking: Whether they can think through the basics like who, what, when, where and injuries.

Do you have a property and casualty license, or would you be interested in earning one?

What they are checking: Their insurance knowledge level and interest in growing in the field.

Practice this interview out loud.

Offer builds a real interview for this exact role at Sentry Insurance from your resume and this job description, asks the questions one at a time, and tells you what landed. The first one is free.

Practice this out loud

The full job description

As published by Sentry Insurance.

Are you a good multi-tasker with great phone skills and enjoy helping others? If you answered yes, you may be a good fit for one of our positions! As a Call Center Representative, you play a critical part in providing services to insureds, claimants, and others relating to the “First Notice of Loss” reports. As Sentry’s promise to be there for our customers during their time of need, you’ll provide technical support for the processing of claims. **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** What You'll Do As a member of Sentry’s Claims Contact Center, you will be the initial point of contact for our customer when an incident occurs. In addition, you will: • Work with a team to successfully meet department phone Key Performance Indicators • Process claims for policyholders, claimants and others over the phone • Assist with processing claims that are received over the internet/mail • Participate in weekly team huddles and associate engagement activities 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 35 consecutive 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 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.