Jobs › Wintrust

Manager, Principal Lending Application Specialist

Wintrust · Rosemont, IL · $140,000–$170,000 a year · Full time

Posted Sep 4, 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

You'd provide third-level support and troubleshoot complex issues. Walk me through a problem that got to you because nobody else could solve it.

What they are checking: Whether they can solve the hardest escalated problems with a real method, since third-level support is where issues land when nobody else can fix them.

You'd provide leadership, mentoring and training and develop best practice procedures. How do you bring a support team up a level?

What they are checking: Whether they can actually develop a support team through mentoring and training, since leading people is half of this senior management role.

What would you do

You'd own the application roadmap, evaluating new releases and functionality. How do you decide whether to take an upgrade?

What they are checking: Whether they weigh the risk and benefit of upgrades carefully, because changes to core lending systems can disrupt the whole bank if handled carelessly.

About the work

This is the most senior application support position for lending systems, based in Rosemont. Which lending applications have you owned?

What they are checking: Whether they have truly owned lending applications at a senior level, because this is the top support role and needs someone who has been accountable.

You'd lead acquisition and conversion activities including data mapping and complex translation tables. Walk me through a conversion you worked on.

What they are checking: The named conversion work, which is where this role earns its keep

You'd review conversion balancing and reconciliation reports. How do you prove a conversion actually landed correctly?

What they are checking: Whether they verify a system conversion with real balancing and reconciliation, because a conversion error can corrupt loan data the bank depends on.

The posting names core banking systems and digital and mobile banking platforms. Which have you worked in, and at what depth?

What they are checking: Whether they are honest about their real depth in core and digital banking systems, so the bank knows where they can lead.

You'd build complex workflows and business process maps. How do you map a process that nobody has written down?

What they are checking: Whether they can uncover and map an undocumented process practically, since building workflows starts with understanding how work really happens today.

You'd do system tuning and optimization. Tell me about a performance problem you fixed.

What they are checking: Whether they can diagnose and fix a real performance problem with evidence, showing they tune systems based on data rather than guesswork.

The posting asks for ten or more years in banking or financial services with emphasis on application implementation and support, plus at least five years of recent management experience. Where do you sit?

What they are checking: Whether their banking, application support and management experience genuinely meets the stated minimums, so both sides know the fit is real.

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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 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? • This position has the opportunity to interface with and have a positive impact on multiple areas of Wintrust's business • We hold ourselves accountable to high standards, share wins, operate ethically, and have fun Position Overview The Principal Application Specialist - Lending is the most senior application support position and serves as a key subject matter expert across the business domains they support. Additionally, this role is the team leader of the IT loan application support team. 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 3 support and troubleshooting of complex issues • Support/Lead acquisition and conversion 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 processes and procedures • Technical application(s) ownership including evaluation new releases/functionality and monitoring application roadmaps and support bulletins Qualifications • 10+ years working in a banking or financial services environment with special emphasis on applications implementation, testing, maintenance, configuration, and support • Minimum of 5 years of recent management experience • Experience building complex workflows and business process maps required • Excellent written and verbal communication skills • Expert level experience in the following technologies or similar a plus: • FIS (Fidelity Information Systems) core banking & financial products & services • Digital and Mobile Banking Platforms • Strong understanding of loan origination, servicing, documentation or other lending technologies and processes. • Payment Processing Systems (Wires, ACH, etc.) • Microsoft technologies (SQL, Azure, Office 365, .NET) • Cisco Networking • Application Programming Interfaces (API) and micro services technologies • Representational state transfer (REST) architecture • Service Oriented Architecture (SOA) • Amazon Web Services (AWS) • Salesforce • ServiceNow • MuleSoft middleware • Oracle, JAVA and Open Source technologies • VBScript or other scripting languages 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 $140,000.00 - $170,000.00, 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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