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This position has closed. Wintrust removed this listing from their careers page on Oct 3, 2026. The interview prep below is still useful, and there are similar open roles at the bottom of this page.

Team Lead Portfolio Management CRE

Wintrust · Chicago, IL · $117,000–$158,000 a year · Full time

Posted Sep 21, 2026 · We last checked this listing on Oct 1, 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 give feedback to an analyst whose work is not good enough yet?

What they are checking: The posting names mentoring by auditing work products and providing feedback.

Tell me about a credit that went bad while you were watching it.

What they are checking: Every portfolio has one, and whether they will name it honestly is the test.

This is in Chicago. How does that fit your life?

What they are checking: Honest fit with the location the posting states.

What would you do

Lending wants a new deal now and your team is behind on annual reviews. How do you set the order?

What they are checking: The posting names assuring new business is prioritized while portfolio management responsibilities are properly managed.

How do you manage a team whose experience levels are very different?

What they are checking: The posting names a team of portfolio managers and credit analysts with varying experience levels.

About the work

Tell me about the commercial real estate credit you have underwritten and which asset classes you know best.

What they are checking: The posting names CRE middle market exposures across various asset classes.

Walk me through reviewing a portfolio manager's underwriting and finding it thin.

What they are checking: The posting names providing a layer of quality control by reviewing work and giving feedback.

How do you assign a risk rating you can defend?

What they are checking: The posting names accurately assigning risk ratings across the portfolio.

How do you test covenants and decide what an exception really means?

What they are checking: The posting names covenant testing and reporting exceptions.

What early warning signs tell you a CRE credit is turning?

What they are checking: The posting names proactively addressing potential concerns.

Practice this interview out loud.

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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 Portfolio Manager Team Lead, Commercial Real Estate manages the administration of a portfolio consisting of CRE Middle Market client credit exposures across various asset classes while managing and prioritizing the workflow of a team of Portfolio Managers and Credit Analysts with varying experience levels. What You’ll Do • Primary responsibilities include assignment, management, and prioritization of ongoing workflow, mentoring Portfolio Managers and Credit Analysts by auditing work products and providing feedback, while contributing to the organizational development of these employees • Serve as the liaison between assigned Lending and Portfolio Management teams assuring new business activities are prioritized while portfolio management responsibilities (renewals, annual reviews, covenant testing, reporting exceptions, documentation exceptions, etc.) are properly managed in accordance with Wintrust Credit Policy • Provide a layer of quality control in the underwriting process by reviewing work and providing feedback to Portfolio Managers and Credit Analysts to ensure analysis and underwriting documents are accurate, risks are properly identified and mitigated, and a structure is in place to appropriately govern the credit based on risk profile • Oversee all portfolio management activities in order to monitor portfolio performance, accurately assign risk ratings, and proactively address potential concerns • Train, mentor, and develop Portfolio Managers and Credit Analysts • Manage quarterly and annual risk reviews • Help drive and support innovation and continuous efficiency improvements Qualifications • Bachelor’s degree in business, finance, accounting or related field • Minimum 7 years’ commercial credit experience with a strong understanding of Commercial Real Estate credit principles, risk management and mitigation, and banking policies/procedures • Prior experience managing a team preferred but not required • Excellent verbal and written communication skills • Strong analytical, organizational, and time management skills • Strong interpersonal skills with a proven ability to establish relationships and work in a team environment 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 $117,000-$158,000 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. 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.