Jobs › Wintrust

Factoring Operations Specialist

Wintrust · Chicago, IL · $50,000–$65,000 a year · Full time

Posted Aug 4, 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

How do you keep accuracy up on repetitive cash application work?

What they are checking: Whether they have real habits that keep accuracy high on repetitive cash work, because small errors repeated at volume become expensive client problems.

Tell me about catching an error before it affected a client.

What they are checking: Whether they can show a real example of catching an error early, which proves attention to detail better than simply claiming to have it.

How do you work with fellow operations specialists so that clients get consistent handling?

What they are checking: Whether they coordinate with teammates so every client gets the same handling, since the posting stresses consistency across the operations team.

This is in Chicago at fifty to sixty-five thousand dollars plus bonus, asking up to five years of factoring, banking or asset-based lending operations experience. What would you want to know about the client portfolio?

What they are checking: Whether they understand the pay, location and experience terms and ask sensible questions about workload, which shows they are weighing the job seriously.

What would you do

You would escalate payment posting issues to a client lead or team lead. What kind of issue would you escalate rather than resolve?

What they are checking: Where their authority ends, which the posting leaves to judgment.

You are the primary operations contact for assigned clients. How do you explain a posting problem to a client who is waiting on funds?

What they are checking: Whether they can explain a posting problem clearly and calmly to a client waiting on funds, keeping trust while the issue gets fixed.

You work to established turnaround times. What do you do when volume exceeds what the day allows?

What they are checking: Whether they triage sensibly and speak up early when volume threatens turnaround times, instead of quietly letting service levels slip for clients.

About the work

This role processes daily client cash receipts for a receivables finance business. Walk me through applying a payment that does not match any open invoice.

What they are checking: Whether they use sound judgment applying cash that doesn't match an invoice, since this daily task decides whether client accounts and funding are right.

How is factoring different from ordinary lending in what the operations team has to get right?

What they are checking: Whether they understand that in factoring the receivable itself is the bank's collateral, which changes what operations must verify and protect every day.

You would alert the portfolio manager to payment irregularities. What kind of irregularity would concern you?

What they are checking: Whether they read the payments or just process them — the real value of the seat.

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.

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 Wintrust Receivables Finance Factoring Operations Specialist works closely with their fellow operations team members to manage all daily cash applications and related responsibilities for the entire WRF client portfolio. This position reports to the Factoring Operations Specialist, Team Lead. What You’ll Do • Work closely with fellow Factoring Operations Specialists to process daily WRF client cash receipts accurately and efficiently in accordance with established turn-around times • Follow established WRF operations policies and procedures for all facets of the Operation Specialist job functions • Escalate payment posting issues and/or client questions to applicable WRF client lead and/or team lead in a timely manner for a prompt resolution • Serve as the primary operations contact for assigned clients • Maintain an effective line of communication with the applicable operations client lead, team lead, and portfolio manager to alert of any payment issues, irregularities or unusual trends observed in performing routine job duties • Maintain a professional and courteous manner with all WRF clients including assisting clients by answering questions and resolving problems promptly • Ensure incoming client emails are put into the correct processing queue and client information is saved properly on the server • Adhere to Bank compliance policies and procedures • Performing all other duties as required Qualifications • Associate’s degree in accounting or related field; Bachelor’s degree a plus • Up to 5 years of Factoring, Banking and/or Asset Based Lending operations experience • Must be detail focused and well organized with the ability to multi-task • Strong interpersonal and customer relation skills required for working with clients and department personnel • Proactive and confident communication skills (both verbal and written) to interact with WRF portfolio and operations colleagues, WRF clients and senior management • Ability to work closely with fellow Operations team members • Strong knowledge of Microsoft Operations applications (specifically MS Excel) with ability to pick up new systems quickly 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 salary range for this role is $50,000-$65,000 , 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.

Apply at Wintrust