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This position has closed. Wintrust removed this listing from their careers page on Sep 28, 2026. The interview prep below is still useful, and there are similar open roles at the bottom of this page.

Factoring Portfolio Analyst

Wintrust · Chicago, IL · $59,000–$77,000 a year · Full time

Posted Sep 14, 2026 · We last checked this listing on Sep 27, 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

How do you talk to a client about a reporting problem without damaging the relationship?

What they are checking: Client handling while holding a control

How do you keep accuracy up when you're reconciling large volumes under time pressure?

What they are checking: Detail discipline at volume, which the posting emphasizes

What would you do

You find a discrepancy between what a client reported and what the documentation shows. What do you do?

What they are checking: Escalation and investigation in a role guarding collateral

What does it mean to manage an account consistent with the account purchase agreement, and what happens when a client wants an exception?

What they are checking: Working inside documented terms rather than accommodating

The role says you work independently with minimal supervision. What do you do when you hit something you're genuinely unsure about?

What they are checking: Independence balanced with knowing when to ask

The posting asks for at least two years in accounts receivable, billing or general accounting with an associate degree, and estimates $59,000 to $77,000 a year. Does that fit?

What they are checking: The stated minimums and pay, confirmed

About the work

This role reviews and reconciles invoice assignment schedules in a factoring portfolio. What do you know about how factoring works?

What they are checking: Whether they understand the product or only accounts receivable generally

Walk me through how you'd review a batch of client invoices for accuracy and compliance.

What they are checking: A real process rather than a description of checking

The posting asks you to alert the relationship manager to unusual trends. What would count as unusual to you?

What they are checking: Pattern recognition rather than task completion

The posting names Excel and mentions Factor Soft or Monarch as a plus. Where are you with each, and how quickly do you pick up new systems?

What they are checking: The stated software requirement, checked

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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 Factoring Portfolio Analyst reviews, analyzes, and reconciles invoice assignment schedules and supporting documentation. In this role, you’ll work closely with the Factoring Portfolio Manager on collateral monitoring, reporting requirements, etc. What You’ll Do • Serve as a point of contact for clients to resolve reporting discrepancies or other collateral-related issues • Process and review invoices submitted by clients for accuracy and compliance • Understand and manage accounts consistent with the Bank approvals and Account Purchase Agreement • Maintain an effective line of communication with the Relationship Manager on assigned accounts, and alert to any unusual trends observed in performing routine job duties Qualifications • Minimum 2 years of direct experience in A/R, billing, or general accounting; banking or asset-based lending operations a plus • Associate degree in accounting or related field; bachelor’s degree a preferred • Must be detail focused and well organized with the ability to multitask • Good interpersonal and customer relations skills are required to deal with clients and department personnel • Proactive/confident communication skills (both verbal and written) to interact with senior management, clients, etc. • Ability to work independently and use independent judgment with minimal supervision • Strong knowledge of Microsoft Office applications (specifically MS Excel) along with ability to pick up on new systems quickly • Experience with Factor Soft or Monarch software a plus 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 $59,000 - $77,000, 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. 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.