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This position has closed. Wintrust removed this listing from their careers page on Sep 25, 2026. The interview prep below is still useful, and there are similar open roles at the bottom of this page.

Collections Rep.-1

Wintrust · Northbrook, IL · $42,000–$55,000 a year · Full time

Posted Sep 15, 2026 · We last checked this listing on Sep 22, 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

The posting says you develop and maintain client relations through superior service. How do you collect from someone and keep them as a client?

What they are checking: The real tension of this job

Tell me about a time you got a late payment in that nobody else could.

What they are checking: Persistence and what they actually did differently

What would you do

You've called and emailed a customer four times with no response. What's next?

What they are checking: Escalation judgment when the usual channels fail

How do you decide when a payment problem is a cash flow issue and when it's something worse?

What they are checking: Reading a situation rather than following a script

This posting is tagged hybrid. How does splitting your week between home and the office work for you in a phone-heavy job?

What they are checking: The stated work pattern, confirmed

The posting prefers one to two years of collections experience and lists an annual salary range of $42,000 to $55,000 plus bonus eligibility. Does that work for you?

What they are checking: Experience level and posted pay, raised before either side invests more

About the work

This is a collections role at FIRST Insurance Funding in Northbrook, monitoring timely payments across a specified region. How do you organize a region's worth of accounts?

What they are checking: A system for working a portfolio rather than a queue

The posting asks for knowledge of accounting principles or finance. How does that help you in a collections job?

What they are checking: Whether they connect the accounting requirement to the work

Walk me through how you'd investigate and verify a return premium.

What they are checking: The specific task named here, and whether they know the sources

What do you do in Excel that makes your collections work faster?

What they are checking: The stated software requirement, tested concretely

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 9 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 • Manages and monitors the timely payments of all accounts in a specified region • Develops and maintains client relations through superior service • Investigates and verifies return premiums as required to expedite the process • Uses various means of communication to collect late payments • Handles miscellaneous projects as required within the portfolio Requirements: • 1-2 years collections experience preferred • Knowledge of accounting principles or finance • Knowledge of Microsoft Word and Excel 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 annual salary range for this role is $42,000- $55,000, along with eligibility to earn annual bonuses. 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.