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Portfolio Manager I - Commercial Real Estate - Chicago

Wintrust · Chicago, IL · $71,000–$92,000 a year · Full time

Posted Sep 24, 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

Tell me about a time you spotted a warning sign on a loan before others did.

What they are checking: Whether they read financials with real curiosity rather than just completing forms.

This is a Portfolio Manager I role. What do you want to learn here over the next two years?

What they are checking: Whether they have a realistic growth path in mind within a promote-from-within culture.

What would you do

An office building loan in Chicago has falling occupancy at renewal. How would you assess the risk?

What they are checking: Their judgment about real current market conditions and how they affect repayment.

A relationship manager wants you to support a loan you're not comfortable with. What do you do?

What they are checking: Whether they can hold a credit view and explain it, even under pressure from sales.

About the work

Walk me through how you analyze a multifamily property's cash flow to decide whether it supports the loan.

What they are checking: Their command of CRE underwriting, including net operating income, vacancy and debt service coverage.

What's the difference between debt service coverage and loan-to-value, and why do both matter?

What they are checking: Whether they understand the two main ways commercial real estate loans are protected.

How do you handle annual reviews and covenant tests across a portfolio of loans?

What they are checking: Their organization in monitoring credit and catching problems before they grow.

How do you review an appraisal and decide whether you trust its value?

What they are checking: Their ability to question assumptions such as cap rates and comparable sales.

What would you look at in a rent roll?

What they are checking: Their attention to lease terms, tenant concentration and rollover risk.

How do you write a credit memo that a committee can read quickly?

What they are checking: Their ability to communicate risk clearly and concisely to decision makers.

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.

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 I, CRE will assist and manage a portfolio of commercial real estate credits/relationships in a fast-paced, regulated environment. The ideal candidate is initiative-taking, has strong analytical and writing skills, and can multi-task across job functions, various client needs and competing bank priorities. What You’ll Do • Provide accurate financial analysis, profitability, and risk assessment to make lending decisions on new, renewal, and extension loans for the following asset types: multifamily, office, medical office, industrial, retail, and self-storage • Create comprehensive, detailed, and thoughtful opportunity memos and full credit approvals for new business clients which will include client and sponsors’ background, history, market experience and global real estate portfolio • Independently analyze credit and financial information of property and individuals to determine the degree of risk associated with the extension of credit • Oversee documentation and ongoing monitoring of asset and client performance • Work with relationship managers and loan administration to facilitate loan closings, modifications, and renewals • Proactively manage covenant compliance testing for existing clients and new clients on an ongoing basis • Review and process construction draws in conjunction with the construction loan administration department, title company and borrower • Work with external and internal business partners on review of deal related legal documents • Develop a working knowledge of credit/loan policy for credit requests and exceptions • Review credit approval memorandums and attorney-prepared loan documents for new and renewed loans to ensure compliance and adherence to the loan approval guidelines • Interact with lending staff, deal teams and clients in a welcoming and professional manner Qualifications • Bachelor’s degree in Business, Finance, Accounting, or Economics • Strong understanding of general credit and risk principles, and banking policies/procedures; formal bank credit training is preferred • Minimum 2 years’ commercial real estate credit, portfolio management and/or commercial lending experience • Strong analytical and business writing skills • Experience with cash flow modeling, lease abstracting and financial statement analysis • Good interpersonal skills with internal partners, counsel, clients and senior management • Accounting and finance knowledge, as well as knowledge of real estate fundamentals and concepts 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 $71,000-$92,000 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.

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