Jobs › Wintrust

This position has closed. Wintrust removed this listing from their careers page on Oct 1, 2026. The interview prep below is still useful, and there are similar open roles at the bottom of this page.

Relationship Associate, Business Banking

Wintrust · Des Plaines, IL · $71,000–$92,000 a year · Full time

Posted Sep 15, 2026 · We last checked this listing on Sep 30, 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

The referrals here come from community bankers and business bankers inside Wintrust. How do you build a relationship with an internal referral source who has no obligation to send you anything?

What they are checking: Internal business development, which this job depends on

Tell me about a deal you declined. How did you handle the relationship afterward?

What they are checking: Holding credit discipline without burning the referral source

What would you do

You'd monitor a tickler report in Moody's for borrower reporting such as financial statements, tax returns and annual site visits. What do you do when a borrower keeps missing their reporting?

What they are checking: Follow-through on covenant monitoring, which is easy to let slide

How do you balance a pipeline of new requests against the servicing work on deals you've already closed?

What they are checking: Time management across two competing demands, called out in the posting

How do you work with credit administration when they want something you think is unnecessary?

What they are checking: Working across the credit boundary without either caving or fighting

About the work

This role generates small business relationships through the Small Business Administration loan programs. What SBA lending have you done?

What they are checking: Specific SBA experience, which is the heart of this job

Walk me through how you evaluate an SBA loan request against both bank loan policy and SBA standard operating procedures.

What they are checking: Command of two rule sets at once, a named duty

How do you assess the risk in an industry you haven't lent to before?

What they are checking: Industry analysis method rather than reliance on a credit score

The posting names fair lending rules including Regulation B, the Fair and Accurate Credit Transactions Act, the Home Mortgage Disclosure Act and the Community Reinvestment Act. Where does a small business lender most easily get that wrong?

What they are checking: Real regulatory awareness, not a list of names

The posting asks for a bachelor's degree or equivalent and two or more years combined in relationship management, lending, commercial underwriting or small business banking. Where do you sit against that?

What they are checking: The stated minimum, confirmed

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 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 The Relationship Associate, Business Banking responsible for providing customized and comprehensive solutions to create value and help meet the strategic priorities and needs for new SBA 7A and Express loans. Including monitoring, analyzing, and providing guidance to internal product partners on post-closing SBA servicing and liquidation activities throughout Wintrust Financial Corporation. In this deadline-oriented role, you will be responsible for managing certain credit relationships – including gathering, analyzing and underwriting all business and personal financial data for the purpose of issuing, extending, amending, and reviewing a commercial credit facility. Responsibilities: • Generate new small business relationships for Wintrust Community Banks and Business Bankers (internal referrals) through utilization of the SBA loan programs and Wintrust treasury management services. • Create and maintain relationships with community bankers and business bankers within Wintrust Community Banks. • Evaluate SBA loan requests using a thorough knowledge of loan policy, guidelines, procedures and SBA standard operating procedures. If appropriate, commence underwriting, SBA eligibility and closing process. • Analyze industries and have a thorough knowledge of risk associated with those industries. Assess the risk inherent in each industry and suggest appropriate financing structures accordingly. • Monitor tickler system report (Moody’s) for accurate tracking and reporting of borrower required reporting including financial statements, tax returns, annual site visits, etc. Takes proactive steps to remedy exceptions always keeping them to a minimum. • Exhibit thorough knowledge of fair lending issues, rules and various regulations that directly impact the commercial lending area (e.g. Regulation B, FACT Act, HMDA, CRA, etc.). • Demonstrate effective time management by balancing multiple priorities within individual workload. • Communicate with and effectively interact with all levels of management, including credit administration personnel, loan operations staff and related departments. Qualifications: • Bachelor’s degree or equivalent • 2+ years combined relationship management/lending, commercial underwriting, small business banking experience is required • Must have excellent time management and organizational skills with an attention to detail • Exceptional written and verbal communication skills, along with interpersonal and customer service skills • Proficiency using Microsoft Office products • Ability to problem solve and comprehend SBA manuals and procedures 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 $71,000 - $92,000, 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.