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Senior Portfolio Manager, CRE

Wintrust · Hartland, WI · $98,000–$132,000 a year · Full time

Posted Sep 4, 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

This role manages a portfolio of commercial real estate credits from Hartland. Walk me through the portfolio you manage now.

What they are checking: Whether they currently manage a commercial real estate portfolio at this senior level and can describe it in specific, confident detail.

What would you do

You'd proactively manage covenant compliance testing. What do you do when a borrower trips a covenant?

What they are checking: Whether they handle a covenant breach with sound judgment and clear steps, because that is when portfolio management stops being routine monitoring.

How do you decide a deal should be declined when the relationship manager wants it?

What they are checking: Whether they will decline a weak deal despite production pressure, because protecting credit quality matters more than keeping one relationship manager happy.

About the work

The posting names multifamily among the asset types. Take one asset type you know well and tell me what you underwrite differently about it.

What they are checking: Whether they have real depth in particular property types, since underwriting multifamily or other assets well takes more than general credit skill.

You'd write opportunity memos and full credit approvals covering the client, the sponsors and their history. What makes a sponsor worth lending to?

What they are checking: Whether they know how to judge a sponsor's track record and strength, because the sponsor often decides whether a real estate loan succeeds.

The posting names cash flow modeling and lease abstracting. Walk me through abstracting a lease and what you pull from it.

What they are checking: Whether they can actually abstract a lease and know which terms matter, since the posting names it and leases drive property cash flow.

You'd review and process construction draws with the construction loan administration department, the title company and the borrower. What goes wrong on a draw?

What they are checking: Whether they know how construction draws go wrong in practice, since coordinating draws with the title company and borrower is a named duty here.

You'd review attorney-prepared loan documents against approval guidelines. What do you look for?

What they are checking: Whether they review loan documents carefully against the approval rather than skimming, because mismatches can leave the bank exposed later.

What would you be watching in commercial real estate right now?

What they are checking: Whether they follow current commercial real estate conditions closely, since this sector is under real pressure and judgment needs to reflect today's market.

The posting asks for a bachelor's degree, at least six years in commercial real estate credit or portfolio management, and prefers formal bank credit training. Where do you sit?

What they are checking: Whether their degree, years of credit experience and training actually meet the stated qualifications, so both sides can judge the fit honestly.

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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 Senior Portfolio Manager, 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 (Business, Finance, Accounting or Economics preferred) • Strong understanding of general credit and risk principles, and banking policies/procedures; formal bank credit training is preferred • Minimum 6 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 $98,000-$132,000, 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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