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Collections Specialist

Wintrust · Rosemont, IL · $20.20–$31.25 an hour · Full time

Posted Aug 4, 2026 · We last checked this listing on Oct 6, 2026

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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

A borrower is clearly struggling but is being honest with you. How does that change your approach?

What they are checking: Humanity within a collections role, which improves recovery as well.

Tell me about a delinquency you resolved without the bank taking a loss.

What they are checking: Concrete recovery experience.

How do you handle the emotional weight of calling people about money they do not have?

What they are checking: Honest self-awareness about a job that wears people down.

This sits in the Managed Assets Division in Rosemont at forty-two to fifty-five thousand dollars plus bonus, asking three years of collections or loss mitigation experience, with some travel and site visits. What would you want to know about the portfolio size?

What they are checking: That they read the terms and ask about caseload.

What would you do

This role collects on past due commercial loans to small businesses. How do you open a call with a borrower who has missed payments?

What they are checking: Tone at the start of a difficult call, which decides how it goes.

You would enforce the bank's legal rights working with outside counsel. How do you decide it is time to stop negotiating?

What they are checking: The judgment that determines recovery and cost.

About the work

You would meet borrowers to formulate loss mitigation plans. What makes a workout plan one the borrower will actually complete?

What they are checking: Realistic plan design rather than a plan that fails in month two.

You would perform site visits to inspect collateral. What do you look for when you get there?

What they are checking: Practical collateral inspection rather than a paperwork visit.

The posting names bankruptcy law among what you need to understand. How does a borrower filing change what you can do?

What they are checking: Real legal knowledge, since the automatic stay changes everything.

How do you keep records of contacts and payment arrangements so they hold up later?

What they are checking: Documentation that supports enforcement and examination.

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The full job description

As published by Wintrust.

Wintrust provides community and commercial banking, specialty finance and wealth management services through its 16 bank charters and nine non-bank businesses. Wintrust delivers the sophisticated solutions of a large bank while staying true to the relationship-focused, personalized service of our community banking roots. We serve clients in all 50 states with more than 200 branch banking locations in Illinois, southwestern Florida, northwestern Indiana, west Michigan and southern Wisconsin and commercial banking offices in Chicago, Denver, Milwaukee, Grand Rapids, Mich., and in key branch banking locations throughout Illinois. Our people are the heart of our business and we are proud to rank consistently as a top place to work. Wintrust is a $66 billion financial institution based in Rosemont, Illinois, and listed on the NASDAQ Global Select Market under the symbol “WTFC.” Why join us? • An award-winning culture! We are rated a Top Workplace by the Chicago Tribune (past 12 years) and Employee Recommended award by the Globe & Mail (past 6 years) • Competitive pay and annual discretionary 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 • Promote from within culture The Collections Specialist is primarily responsible for managing and collecting on past due Community Banking Commercial Loans (CBCL) within the Managed Assets Division. This role plays a critical part in mitigating risk and reducing losses for the bank by implementing effective loss mitigation strategies, maintaining detailed records, and ensuring compliance with regulatory standards. This position involves regular communication with delinquent borrowers, negotiation of repayment plans, and coordination with internal stakeholders and external counsel. What You’ll Do • Make outbound collection calls on delinquent consumer and small business loans • Work directly with borrowers to address concerns, negotiate resolutions, and bring delinquent accounts current • Document all communication and financial updates accurately in the bank's system including attempted contacts and payment arrangements • Enforce the Bank’s legal rights and remedies, working closely with outside counsel and third-party professionals to manage litigation and related legal proceedings • Partner with Team Lead and/or Loan Officer to identify, evaluate, and address potential concerns and issues • Occasional travel and site visits to inspect collateral may be required Qualifications • High school diploma or GED • Minimum 3 years’ collections and/or loss mitigation experience • Prior experience with a financial institution strongly preferred • Familiarity with standard lending disclosures, privacy rules, and debt collection compliance • Excellent verbal and written communication skills with the ability to handle difficult conversations with empathy and firmness • Strong judgment, problem-solving capabilities, and active listening skills to handle complex, non-routine financial matters • Proficient in Microsoft Office applications (specifically 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 hourly rate for this role is $20.20 to $31.25, 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-AC1 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.

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