Jobs › Wintrust

Contact Center Rep. 1

Wintrust · Northbrook, IL · $17.31–$22.60 an hour · Full time

Posted Oct 2, 2026 · We last checked this listing on Oct 6, 2026

Apply at Wintrust

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 turned around an upset customer.

What they are checking: Whether they have real experience calming customers and solving their problem.

How do you handle a high volume of calls without getting worn down?

What they are checking: Whether they have habits to stay positive and focused in a busy contact center.

What would you do

You'd handle both incoming calls and web chats. How do you keep quality high when switching between them?

What they are checking: Whether they can manage different channels without losing accuracy or tone.

A caller is angry because they received a notice that their insurance policy may be canceled for nonpayment. How do you handle the call?

What they are checking: Whether they stay calm, explain the situation clearly and help the customer find a solution fast.

An insurance agent calls asking about a customer's account. What can you share?

What they are checking: Whether they understand who is authorized to receive information, since agents are key partners.

You don't know the answer to a caller's question. What do you do?

What they are checking: Whether they find the right answer or escalate instead of guessing.

About the work

FIRST Insurance Funding helps customers finance their insurance premiums. How would you explain premium financing to a caller who doesn't understand their bill?

What they are checking: Whether they can grasp the product and explain it simply to confused customers.

How do you verify a caller's identity before discussing their account?

What they are checking: Whether they protect customer information and follow security steps every time.

How do you stay accurate when taking a payment over the phone?

What they are checking: Whether they double-check payment details, since mistakes cause missed payments and cancellations.

How comfortable are you using several computer systems at once while talking with a customer?

What they are checking: Whether they can multitask in systems smoothly, which keeps calls short and accurate.

Practice this interview out loud.

Offer builds a real interview for this exact role at Wintrust 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 Wintrust.

As one of the largest premium finance companies in the country, FIRST Insurance Funding provides full premium finance services, plus additional services built specifically for agencies. We pride ourselves on the variety of incentive programs, services, and technology we offer. This not only helps grow the agents, brokers, and companies we partner with, but also helps them better serve their clients. FIRST Insurance Funding is a subsidiary of Wintrust, a financial services company with more than $66 billion in assets. Why join us? • An award-winning culture! We are rated a Top Workplace by the Chicago Tribune (past 8 years) and Employee Recommended award by the Globe & Mail (past 6 years) • Competitive pay and discretionary or incentive bonus eligible • Comprehensive benefit package including medical, dental, vision, life, a 401k plan with a generous company match and tuition reimbursement to name a few • Family-friendly work hours • With 175+ community bank locations, we offer opportunities to grow and develop in your career • Promote from within culture Why join this team? • We have a culture that encourages an entrepreneurial spirit • We offer multiple opportunities for development and upward mobility What You’ll Do: • As a Customer Service Representative, you will be responsible for answering incoming calls/web chats and assisting customers by providing information or resolving issues. • Researching and analyzing transactions and other account issues. • Entering or modifying Check-By-Phone payments Qualifications: • 1+ years customer service experience - ability to work 10:00am to 7:00m shift • Prior call center or finance experience is preferred • High school diploma or equivalent, some college preferred • Basic computer skills, PC, Microsoft Word/Excel & Internet • Excellent interpersonal skills and the ability to effectively interact with people of all skill levels and diverse backgrounds Benefits: Medical Insurance • Dental • Vision • Life insurance • Accidental death and dismemberment • Short-term and long term Disability Insurance • Parental Leave • Employee Assistance Program (EAP) • Traditional and Roth 401(k) with company match • Flexible Spending Account (FSA) • Employee Stock Purchase Plan at 5% discount • Critical Illness Insurance • Accident Insurance • Transportation and Commuting Benefits • Banking Benefits • Pet Insurance Compensation: The estimated hourly salary range for this role is $17.31 to $22.60 along with eligibility to earn an annual bonus. Actual salaries may vary based on several factors, such as a candidate’s qualifications, skills, and experience. #LI-HYBRID From our first day in business, Wintrust has been proud to serve a variety of unique communities and people from all walks of life. To build a company that reflects the communities we serve, we believe that fostering a unique and inclusive workplace where everyone feels valued and empowered to succeed will support our ongoing success. Wintrust Financial Corporation, including community banking and financial services subsidiaries, is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, age, national origin, disability, veteran status, genetic information, and other legally protected categories.

Apply at Wintrust