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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

Wintrust · Rosemont, IL · $20.19–$26.00 an hour · 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

You're asked to document all communication with internal and external parties. Why does that matter in collections?

What they are checking: Whether they understand documentation as protection, not paperwork

Tell me about a discrepancy you investigated where the first explanation turned out to be wrong.

What they are checking: Research persistence, a stated duty

What would you do

Walk me through how you'd handle a customer whose insurance policy is about to cancel for non-payment.

What they are checking: Urgency and the ability to prevent the cancellation rather than just record it

You call a delinquent customer and they get hostile. What do you do?

What they are checking: Staying professional and within collection rules under pressure

The posting names minimizing loan aging and exposure. How do you decide which accounts to work first on a busy day?

What they are checking: Prioritizing by exposure rather than by ease

The posting is tagged onsite, prefers one to two years of collections experience, and estimates an hourly rate of $20.19 to $26.00. Does that fit what you're looking for?

What they are checking: Work pattern, experience level and posted pay, confirmed

About the work

This is a collections role at FIRST Insurance Funding in Rosemont, managing a regional premium finance portfolio. What's your experience with loan servicing?

What they are checking: Whether they know premium finance or only general collections

The job includes contacting insurance carriers and general agents to confirm cancellation and obtain return premium amounts. What slows that process down, and how do you keep it moving?

What they are checking: Knowledge of the return premium chase, the main lever on aging

How do you verify an unearned premium figure you've been given?

What they are checking: Whether they check numbers or accept them

How do you use Excel in a collections job? Give me a specific example.

What they are checking: The stated software requirement, tested with evidence

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.

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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 11 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 200+ 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 The Collections Rep will Manages a regional/specialty premium finance portfolio. Overseeing all aspects of loan servicing, including but not limited to, service requests, proactive communication, post cancellation activities, and resolving loss shortages. Provides internal/external superior customer service working closely with borrowers, insurance carriers/general agents, and insurance agents. Job Description • Processes all incoming service requests, including researching and investigating discrepancies, documents all communication with internal and external parties, and processes loan updates and adjustment in the loan management system. Manage regional/specialty portfolio by preparing, analyzing and/or monitoring daily reports and prioritizing daily tasks to manage portfolio performance. Develop and maintain effective relationships with agents and other external/internal parties. • Minimize loan aging and exposure/shortages by contacting insurance carriers and general agents to confirm cancellation and obtain return premium amounts. Verifies unearned premium credit (i.e. collateral), investigate discrepancies, and follows up for receipt of funds. • Timely communicate delinquent payment information to customers via phone and email in an attempt to prevent loan / policy cancellations and aging. • Handles miscellaneous tasks and projects as required within the portfolio. Requirements • 1-2 years collections experience preferred • Knowledge of basic mathematics • Knowledge of Microsoft Word and Excel Compensation The estimated hourly rate for this role is $20.19 - $26.00 along with eligibility to earn an annual bonus. Actual pay rate may vary based on several factors, such as a candidate’s qualifications, skills and experience 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 #LI-ONSITE #LI-LR1 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.