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Commercial Draw Analyst

Wintrust · Rosemont, IL · $50,000–$70,000 a year · Full time

Posted Sep 24, 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

Tell me about a time you caught an error in a disbursement or budget before it went out.

What they are checking: Whether their attention to detail has actually protected money, not just whether they claim to be careful.

Tell me about a time you had to tell someone senior that a request didn't meet policy.

What they are checking: Whether they will hold a control line with a banker who outranks them and explain it without friction.

What would you do

The inspector says the project is 40 percent complete but the borrower has billed for 60 percent. What do you do?

What they are checking: Whether they will hold funds and escalate when the work does not support the request, even under pressure.

How do you handle a contractor who calls you directly every day asking when their money will arrive?

What they are checking: Whether they can stay courteous and clear about process while not letting pressure shortcut the review.

You have twelve draws due this week and two relationship managers each say theirs is the most urgent. How do you sort it out?

What they are checking: How they prioritize fairly by deadlines and risk instead of by who pushes hardest.

About the work

Walk me through how you process a construction draw request from the moment it lands until funds go out.

What they are checking: Whether they know the full control sequence, from inspection to title update to disbursement, and where errors slip in.

What do you check on a draw request before you'd let a dollar be released?

What they are checking: Whether they verify lien waivers, inspection reports, budget lines and remaining funds instead of just matching totals.

What does it mean for a construction loan to be out of balance, and why does it matter?

What they are checking: Whether they understand that remaining loan funds must cover the cost to complete or the bank is exposed.

Why do conditional and unconditional lien waivers matter, and when do you need each?

What they are checking: Whether they understand mechanics lien risk and how waivers protect the bank's first lien position.

How do you keep track of retainage, change orders and title date-downs across many open projects?

What they are checking: Whether they have a real tracking system that would hold up across dozens of active construction loans.

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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 9 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 Why join this team? • We are a high performing, collaborative, and diverse team focused on transforming the business through engaging work on enterprise-wide product innovation • We are a vibrant, team-oriented atmosphere that provides opportunities for individual growth; • We are seeking a critical thinker that’s willing to learn and not afraid of taking on new initiatives. • Gain experience and further your career by joining a growing organization What you'll do: • The Commercial Draw Analyst will primarily be responsible for supporting the monitoring and risk management of commercial and residential construction loans and draw requests. • The primary function of this role is to support the Commercial Draw Managers in reviewing post-closing construction draw requests, as well as facilitating pre-close document collection and third-party cost/documentation reviews. • The Commercial Draw Analyst will be responsible for collecting and reviewing pre-close due diligence documentation and post-close construction draw request documentation. • This includes ordering and reviewing professional reports such as title endorsements, inspection reports, and certificates of insurance, as well as various administrative tasks as needed. • The Commercial Draw Analyst will also be expected to enter draw requests into the departments’ draw processing software for final review by the Commercial Draw Managers. Qualifications: • 3-5 years of relevant experience. • Advanced computer skills. Must be highly proficient with MS Excel. • Ability to thrive in a high-volume role, handling many varied tasks for multiple projects and colleagues in a given day. • Must be self-motivated to meet deadlines. • Experience with a financial institution, Title Company, real estate developer, and/or with a general contractor is a plus. • Experience in commercial construction loan underwriting/funding/disbursement experience is a plus. • Experience with construction funding software program(s) a plus. • Understanding of basic construction processes and risks is a plus. • Ability to communicate with, collaborate with, and support several different stakeholders, including Colleagues, borrowers/clients, lending and credit teams, contractors, inspectors, title companies, etc. 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 $50,000-$70,000, 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-HYBRID 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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