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This position has closed. Wintrust removed this listing from their careers page on Sep 29, 2026. The interview prep below is still useful, and there are similar open roles at the bottom of this page.

Senior Commercial Loan Closing Specialist - Milwaukee Area

Wintrust · Milwaukee, WI · $59,000–$77,000 a year · Full time

Posted Sep 10, 2026 · We last checked this listing on Sep 28, 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 keep several closings moving at once without one slipping?

What they are checking: Prioritization, a stated requirement

What would you do

You find a document that doesn't match the approval two days before closing. What do you do?

What they are checking: Holding a closing against schedule pressure

How do you manage a closing pipeline and keep lenders, title companies and attorneys all on the same timeline?

What they are checking: Coordination across parties who don't work for you

A lender is pushing to close before something is in place. How do you handle that?

What they are checking: Where their line sits against revenue pressure

The salary range is $59,000 to $77,000, based in the Milwaukee area. Does that work for you?

What they are checking: Posted pay and location, raised plainly

About the work

This role closes more complex middle market and commercial real estate loans in the Milwaukee area. Walk me through a closing you managed from approval to funding.

What they are checking: End-to-end closing ownership rather than document collection

The posting names title work, flood and sanctions searches, insurance, organizational documents and real estate collateral documentation. Which of those most often holds up a closing, and how do you get ahead of it?

What they are checking: The specific documents named and where they go wrong

How do you review a credit approval memorandum against attorney-prepared loan documents to make sure they match?

What they are checking: The core control in this job

Walk me through how you make sure loan proceeds and costs are applied correctly at closing.

What they are checking: Funding accuracy, where errors cost real money

The posting asks for a high school degree and five or more years of commercial and industrial or commercial real estate loan closing experience. Where do you sit?

What they are checking: The stated minimum, confirmed

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 • With 175+ community bank locations, we offer opportunities to grow and develop in your career • Promote from within culture Position Overview: The Senior Commercial Loan Specialist facilitates the loan closing process for more complex and larger Middle Market Commercial Lending and Commercial Real Estate lines of business by serving as a liaison between lenders, external legal counsel, title insurance representatives and loan operations during all aspects of loan documentation from the time legal counsel is engaged through the end of the loan closing process. What you will be doing: • Obtains appropriate supporting documents including title work, flood and OFAC searches, insurance, organizational documents, real estate collateral documentation and various due diligence items to verify compliance with loan approval and bank closing procedures. Verification of larger/more complex document checklist ensuring accuracy and timing measures completed. • Reviews credit approval memorandum and attorney-prepared loan documents only for new and renewed loans to ensure compliance and adherence to the loan approval guidelines. Interfaces independently with outside counsel. • Manages the loan closing pipeline and communicates timelines with internal loan operations department, lenders, title companies, and attorneys throughout the loan process. • Coordinates the application of loan deposits and disbursement of loan proceeds to ensure funds are applied correctly and all costs and invoices as paid at loan closing. Qualifications: • High school degree or equivalent. • 5 plus years of C&I or CRE Loan Closing experience. • Excellent oral and written communications skills. Strong analytical, organizational and time management skills. Proven ability to manage tasks in a timely and efficient manner. • Advanced computer skills. • Ability to proactively manage and prioritize work flow. 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 $59,000 - $77,000, 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.