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Portfolio Manager II, CRE

Wintrust · Willowbrook, IL · $85,000–$110,000 a year · Full time

Posted Sep 10, 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

How do you write an approval memo that gives a committee what it needs to decide?

What they are checking: Whether they write approval memos that give a credit committee exactly what it needs, because clear writing is a stated requirement and drives decisions.

What would you do

You'd manage covenant compliance testing on an ongoing basis. What do you do when a borrower trips a covenant?

What they are checking: Response to a covenant breach rather than just noting it

A relationship manager wants a structure you think carries too much risk. How do you handle that?

What they are checking: Whether they can hold a sound credit view when a relationship manager pushes back, protecting the bank without damaging the working relationship.

About the work

This role manages a portfolio of commercial real estate credits from Willowbrook. Which asset types have you underwritten?

What they are checking: Whether they have underwritten the range of property types this portfolio holds, since each commercial real estate asset type carries different risks.

Walk me through how you build a cash flow model for an income-producing property.

What they are checking: Whether they can build an income property cash flow model themselves, because the posting requires modeling and it drives every credit decision here.

The posting names lease abstracting. What do you pull out of a lease that changes your view of the credit?

What they are checking: A specific skill that separates real estate lenders from general commercial ones

How do you assess a sponsor as opposed to the property itself?

What they are checking: Sponsor analysis, which the posting names in the approval memo

Walk me through reviewing and processing a construction draw.

What they are checking: Whether they understand how construction draws are reviewed and released, since paying a draw too early or wrongly puts the bank's money at risk.

What do you watch in a real estate portfolio to spot deterioration before the financials show it?

What they are checking: Whether they watch for early warning signs of property trouble, because catching deterioration before the financials show it gives the bank time to act.

The posting asks for a bachelor's in business, finance, accounting or economics, at least four years of commercial real estate credit or lending experience, and prefers formal bank credit training. Where do you sit?

What they are checking: Whether their degree, credit experience and training genuinely match the stated qualifications, so both sides can judge the fit honestly from the start.

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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 matches and tuition reimbursement to name a few • Family-friendly work hours • Promote from within culture The Portfolio Manager II, 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 4 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 $85,000-$110,000, 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.

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