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This position has closed. Wintrust removed this listing from their careers page on Sep 30, 2026. The interview prep below is still useful, and there are similar open roles at the bottom of this page.

Loan Documentation Administrator Sr

Wintrust · Rosemont, IL · $59,000–$77,000 a year · Full time

Posted Aug 10, 2026 · We last checked this listing on Sep 29, 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

You assist in guiding and training team members. What do people new to loan documentation most often get wrong?

What they are checking: Depth visible through what they teach.

This is a senior seat in Rosemont asking three to five years on very complex and high dollar commercial and commercial real estate transactions, supporting several Wintrust charters. What would you want to know about the volume and the mix?

What they are checking: That they ask what the actual book looks like.

What would you do

You confirm a loan's structure can be accommodated on the loan systems. Tell me about a structure the system could not handle and what you did.

What they are checking: The specific bridge between legal documents and bank systems that this role owns.

You decide when to reach out to counsel for guidance. Where is that line for you?

What they are checking: Judgment about their own limits, which the posting leaves to them.

A lender is pushing to close and a due diligence item is not complete. How do you handle it?

What they are checking: Holding a documentation requirement against production pressure.

When would you escalate to a chief credit officer rather than resolving it yourself?

What they are checking: Escalation judgment at a level where they have real discretion.

About the work

This role prepares LaserPro documentation and reviews attorney-prepared documents for complex transactions. What do you look for first in an attorney-drafted loan document?

What they are checking: Review method on documents someone else wrote, the senior part of this job.

The posting names capital call lines, leveraged loans, institutional, government and municipal, and franchise lending. Which of those have you documented, and what makes each different?

What they are checking: Real breadth across the named transaction types rather than general loan operations.

You complete post-closing review to confirm due diligence and executed documents are present, and identify trailing exceptions. What is most often missing after a closing?

What they are checking: Firsthand knowledge of where files come up short.

You analyze real estate tax bills to set monthly escrow and the beginning balance. Walk me through that calculation.

What they are checking: A specific and checkable technical task named in the duties.

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.

Practice this out loud

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 10 years) and Employee Recommended award by the Globe & Mail (past 6 years) • Competitive pay and discretionary or incentive 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 Why join this team? • We have a culture that encourages an entrepreneurial spirit • We offer multiple opportunities for development and upward mobility What you'll do: The Loan Documentation Administrator Sr. position is responsible for preparation of LaserPro loan documentation and the review of attorney prepared documents for complex and multi-million-dollar commercial loan transactions including option-based pricing loans, Swaps, Syndications, Participations, First Insurance transactions, Capital Markets, Capital Call Lines, Leveraged Loan Transactions, Institutional loans, Government and Municipal lending, Franchise lending, Wintrust Business Credit monitored loans, international transactions and commercial real estate transactions. • Additionally, this position reviews same transactions post-closing ensuring that all due diligence and executed loan documents are present, identify trailing documentation exceptions and prepare the file for Servicing • Review complex attorney prepared documents for lending groups ensuring that the structure of the loan can be accommodated on loan systems. • Appropriately enforce all corporate due diligence and compliance requirements. • Communicate effectively with lender and/or lending support staff regarding issues, questions or additional information needed during the documentation preparation and/or attorney review stage to ensure that Loan Operations and the lending staff are working together to meet borrower needs. • Seek attorney assistance on questions/issues arising from both preparation and review of loan documents. Determine when it is necessary to reach out to counsel for guidance and assistance with questions as well as request and utilize specialized language as needed to protect Bank’s interest in the loan transaction. • Seek guidance of Bank’s Chief Credit Officers at appropriate times to assist in clarification of loan transactions. • Complete post-closing review of documentation to ensure due diligence document requirements have been completed and executed loan documents are present. • Identify trailing documentation exceptions for entry by Collateral team. • Prepare the final file for booking and funding. • Complete analysis of real estate tax bills to determine monthly escrow payments as well as beginning balance for real estate transactions. • Assist in providing guidance and training to team members as need arises. Qualifications: • Minimum 3-5 years of experience preparing/reviewing very complex and high dollar commercial and commercial real estate loan transactions. • Strong understanding of commercial lending concepts and experience in a loan operations environment handling and supporting commercial lending staff. • Excellent knowledge and understanding of collateral perfection requirements, commercial loan documents, corporate credit policy, approval levels, the workings of a larger loan operations group and some basic loan accounting knowledge and audit controls. • Wide experience level of commercial real estate and the more complex workings of real estate lending and working with title companies. • Superior communication skills (both written and verbal) and the ability to partner with commercial lenders and support staff to ensure that transactions are completed satisfying both Bank requirements and customer expectations. • Ability to determine appropriate level of flexibility in procedures and policies to assist lenders in closing loan transactions. Strong use of common-sense approach to assisting lending staff. 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 $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. #LI-Onsite 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.