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Commercial Real Estate Banker II

Wintrust · Rosemont, IL · $98,000–$132,000 a year · Full time

Posted Jul 23, 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

Walk me through how you'd build a pipeline of commercial real estate prospects in the Chicago market from a standing start.

What they are checking: Whether they have a repeatable prospecting method or just wait for referrals to show up on their desk.

Tell me about a CRE deal you closed that almost fell apart. What saved it?

What they are checking: How they handle late surprises like appraisal gaps or environmental findings without losing the client or the bank's protections.

Tell me about a time credit declined or restructured a deal you believed in. How did you handle it with the client?

What they are checking: Whether they can deliver bad news honestly and keep the relationship without blaming the bank's credit team.

Where do your referrals come from today, and how would you widen that network around Rosemont and Chicago?

What they are checking: Whether they already have ties to brokers, attorneys and developers that can feed new business.

What would you do

Office vacancy is up and your borrower's anchor tenant just gave notice. What do you do in the first week?

What they are checking: Whether they get ahead of a deteriorating credit with the borrower and credit team instead of hoping it resolves.

How do you decide when a prospect isn't a fit for a community bank like Wintrust and should go elsewhere?

What they are checking: Whether they protect the bank's risk appetite and their own time instead of forcing every deal through.

Wintrust wants deposits and treasury services along with the loan. How do you bring that into a real estate conversation?

What they are checking: Whether they treat relationships as full banking relationships rather than one-off loans that bring no deposits.

About the work

A developer brings you a multifamily construction deal. What are the first numbers you look at to decide whether it's worth taking to credit?

What they are checking: Whether they can screen a deal quickly on debt service coverage, loan to value and sponsor strength before wasting anyone's time.

How do you explain the difference between loan to cost and loan to value to a borrower who thinks they should get the higher number?

What they are checking: Whether they understand construction lending math well enough to teach it calmly to a client who wants a different answer.

What do you look for in a sponsor's real estate schedule and global cash flow?

What they are checking: Whether they can spot a sponsor who is overleveraged across other properties even when this one deal looks clean.

How do you stay current on cap rates, rents and construction costs across the property types you lend on?

What they are checking: Whether their market knowledge is current enough to challenge a borrower's pro forma rather than accept it.

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 What You’ll Do: • Responsible for developing new prospects, managing and growing a portfolio of existing commercial real estate relationships. • Experience in variety of real estate transactions including multifamily, retail, industrial, office, self-storage, land development and commercial construction loans. • Experience with maintaining and managing a portfolio, with ability to build relationships with existing and prospective customers focusing on revenue growth, fee income, deposits and cross-selling services • Participation and knowledge within loan syndications and maintaining those relationships • Network with variety of CRE COI’s, investors and attorneys to establish a referral base. • Prepare, review and present credit memos to senior management while maintaining structures within credit guidelines. • Prepare and present deal terms to clients in a timely and accurate manner. • Oversee the review and underwriting of credit requests internally while making recommendations for approval to senior management. • Provide leadership in the development of less experienced commercial real estate lenders and portfolio managers. Qualifications: • Bachelor’s degree in business, finance, economics, accounting or equivalent direct banking experience. • Minimum 3-5 years of credit and commercial real estate lending experience combined • Solid understanding of general credit and risk principles, and banking policies/procedures; formal credit training is preferred • Exceptional written, verbal, negotiation, and presentation skills • Excellent analytical and organization skills with the ability to prioritize workflow Proficient with Microsoft Office • Demonstrate high ethical standards and personal integrity 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 $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. 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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