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Manager, Senior Application Specialist - IT Lending Support

Wintrust · Rosemont, IL · $125,000–$145,000 a year · Full time

Posted Aug 25, 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

Wintrust runs sixteen bank charters and this role supports acquisitions. Walk me through a conversion you worked on. What did the data mapping get wrong the first time?

What they are checking: Real conversion experience, which this role is explicitly asked to support or lead.

Tell me about a vendor release you evaluated and decided to delay. What made you hold?

What they are checking: Application ownership judgment rather than taking every upgrade.

Describe a process improvement you took to a line of business. How did you get them to change how they worked?

What they are checking: Influence over a business team the manager does not control.

This is a Rosemont role asking for seven to ten years, with lending solutions, international systems and interface work all in scope. What do you want to know about the size of the team and how much of the year goes to acquisition conversions?

What they are checking: Whether they ask what the real workload mix is before accepting.

What would you do

This supports lending applications on a core banking platform. Walk me through how you handle a level two ticket where the business says the balance is wrong and the system says it is right.

What they are checking: Troubleshooting method on the kind of complex issue this role escalates to.

Conversion balancing reports do not tie. How do you work that?

What they are checking: Reconciliation discipline at the point where a conversion succeeds or fails.

You are mentoring a specialist who is technically fine but keeps closing tickets the business reopens. What do you do?

What they are checking: Developing judgment rather than skill, which is the harder coaching problem.

About the work

The posting names nCino, Credit Lens, Laser Pro, Dealer Portal and Factor Soft. Which of those have you actually supported, and what broke most often?

What they are checking: Honest depth across the specific lending systems named.

How do you build a translation table that does not fall over on the edge cases nobody mentioned in requirements?

What they are checking: The complex translation table work this posting names, judged by handling of exceptions.

How do you tune an application when the business says it is slow but you cannot reproduce it?

What they are checking: Performance diagnosis without a reproducible case.

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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 • 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 • Promote from within culture Why join this team? • We hold ourselves accountable to high standards to be “Best in Class” while sharing wins, operating ethically, and have fun in a friendly atmosphere Position Summary The Manager, Senior Application Specialist is a senior level position and serves as a subject matter expert across the business domains they support. They are accountable for ensuring the day to day operations of the systems under their charge and for supporting and implementing change and configuration management, including testing and defect management relating to new product implementations, development releases, upgrades, patches, and other system maintenance as required. Application Specialists will work closely with Business resources and stakeholders, internal Technology teams, and various vendors and third-party consultants and implementers. They must understand their application’s interdependencies with other applications and infrastructure both internally and outside the corporate network. Ongoing knowledge of current and changing business and technological environments, trends and strategy is important to success. This position will also support/lead acquisition and conversion activities related to their business domains. What You’ll Do • Handling of day-to-day workflow (monitoring ticket system, e-mail, daily tasks, ongoing training) and Level 2 support and troubleshooting of complex issues • Support/Lead project activities including data mapping, completion of complex translation tables, reviewing conversion balancing and reconciliation reports, implementation of a new application, system functionality or integration. • Supporting line of business process improvement and efficiency initiatives • System tuning and optimization • Supporting change management and product/project implementation • Provide leadership, mentoring and training and develop best practice process and procedures • Technical Application(s) Ownership including evaluating new releases/functionality and monitoring application road maps and support bulletins Qualifications • 7-10 years of relevant experience with an emphasis on applications implementation, testing, maintenance, configuration, releases, upgrades, new products and support including creation of test plan and documentation of results • Ability to analyze, learn, and apply rapidly changing technologies, and apply them as part of integrated solutions to business requirements. • Able to work with strict deadlines and time pressure • Advanced level experience in the following technologies or similar a plus: • FIS (Fidelity Information Systems) core banking & financial products & services. CLS/ACBS experience a plus! • Lending Solutions such as nCino, Moody’s Credit Lens, Dealer Portal / Shaw, Laser Pro, and Factor Soft experience. • International Services systems such as CIBAR. • Application Programming Interfaces (API) and micro services technologies • Salesforce • ServiceNow • VBScript or other scripting languages • Previous team supervisory leadership experience within the past 5 years is preferred 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 $125,000.00 - $145,000.00, 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 #LI-JB1 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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