Jobs › Wintrust

Senior IT Project Manager

Wintrust · Rosemont, IL · $98,000–$132,000 a year · Full time

Posted Sep 3, 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

This role runs information technology projects end to end from Rosemont, at assistant vice president level. Walk me through the largest project you have owned.

What they are checking: Whether they have truly owned large IT projects end to end, since this assistant vice president role needs someone accountable for results, not coordination.

A project is going to miss its date. When and how do you say so?

What they are checking: Whether they flag a missed date early and honestly, because surprising stakeholders late is what most damages a project manager's credibility.

You'd mentor the team on project artifacts — plans, statements of work, status reports. What makes a status report useful rather than a formality?

What they are checking: Whether they hold a real view on what makes project artifacts useful and can teach it, since mentoring on them is a stated duty.

What would you do

You'd prepare budget submissions and change requests. How do you handle a scope change that nobody wants to pay for?

What they are checking: Whether they manage scope changes through proper change control even when nobody wants to pay, which protects the budget and the schedule.

The posting names technology governance and architecture alignment. What do you do when a project team wants to build something outside the standard?

What they are checking: Whether they will hold the architecture and governance standard when a team wants to work around it, since a bank depends on consistent technology.

You'd build relationships across business, technology, compliance, legal and external partners. How do you get a compliance review done on your timeline?

What they are checking: Whether they can work effectively with compliance, legal and other bank stakeholders to keep reviews on schedule without burning goodwill.

You'd take part in recruiting and onboarding project office staff, consultants and temporary workers. How do you bring a consultant up to speed fast?

What they are checking: Whether they can onboard consultants and temporary staff quickly and well, since this duty takes real time and affects how fast projects move.

About the work

How do you plan a project when the requirements are still forming?

What they are checking: Whether they can plan sensibly while requirements are still changing, because most real projects start before every detail is known.

You'd track project actuals against budget and validate receipt of goods before authorizing invoice payments. How do you keep a project's spending honest?

What they are checking: The financial control duty, which many project managers skip over

The posting asks for five to ten years of related experience and prefers financial services or financial systems at a mid to large organization. Where do you sit?

What they are checking: Whether their experience fits the stated range and preferred financial services background, so both sides understand the fit from the start.

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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 8 years) and Employee Recommended award by Globe & Mail (past 6 years) • Competitive pay and 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 • Promote from within culture Why join this team? • We hold ourselves accountable to high standards, share wins, operate ethically, and have fun • This role offers the ability to make an impact and interface with IT and the various aspects of Wintrust’s businesses What you’ll do: The Senior IT Project Manager / Assistance Vice President (AVP) orchestrates the initiation, planning, execution, monitoring and closing of projects with a specific term that have a beginning, an end and specified technology deliverables. The IT Senior Project Manager is responsible for communicating and integrating IT activities into the broader plan held with the business unit/s. The Senior IT Project Manager acts as primary point of contact for project stakeholders across IT, IS, and IT vendors. The Senior IT Project Manager provides technology artifacts to support the movement of projects / programs through the Enterprise Project Management Office (ePMO) governance process including ePMO processes, templates and Project Portfolio Management (PPM) Clarity tool updates. The Senior IT Project Manager defines and maintains project plans, inclusive of scope, milestones, dependencies and technology deliverables. The Senior IT Project Manager is expected to have exposure to enterprise architecture, core banking systems, SaaS applications framework. The Senior IT Project Manager creates, manages and reports on projects / programs, technology, financials and budget. Projects may vary in number, size and complexity. Generally, manages moderate to high complexity, large to extra-large sized projects. Key Accountabilities: • Project Ownership • Project Life Cycle: • Plan the Project • Execute the Project • Monitor and Control the Project • Close the Project • Technology Governance & Architecture Alignment • Efficiencies / Continuous Improvement • Other Duties, as assigned • People: • Participate in the recruiting and hiring of IT PMO staff, consultants and temp workers with appropriate skills • Take part to onboard new team members to the IT PMO team, Wintrust Technology and Wintrust Corporation • Mentor the team in the creation of all project artifacts, including project plans, statements of work, status reports, etc. • Build and maintain influential relationships across business, technology, compliance, legal, and external partner organizations. Qualifications: • 5-10 years of related experience • Financial Services or Financial systems at mid-to-large organizations experience, preferred • Bachelor’s degree or equivalent • Resolve non-routine problems • Exercise judgement within defined procedures and practices • Require minimum supervision • Track project actuals vs. budget. Validate receipt of goods/services before authorizing invoice payments. Prepare project budget submission and change requests, as needed • Accountable for project with broad scope • Project Management Professional (PMP) certification, Program Management Professional (PgMP), or PMI Agile Certified Practitioner (PMI-ACP), preferred • Certified ScrumMaster (CSM) or Professional Scrum Master (PSM II/III), preferred • Experience with one or more project management tools (Clarity preferred) • Good technology knowledge, understanding and experience leading technology projects / programs. • Ethical behavior and business practices • Communication: Speak, listen and write in a clear, thorough and timely manner. Comfortable talking with all levels of management • Strong interpersonal, organizational, attention to detail and follow-up skills • Identify and communicate issues early. Bring recommendations and options to resolve issues • Foster teamwork: Work cooperatively and effectively with others to set goals, resolve problems and make decisions • Leadership skills: Positively influence others to achieve results • Make decisions: Assess situations to determine importance, urgency and risks to produce clear decisions. Raise issues to Sr. management • Organizational skills: Set priorities, develop work schedule and monitor progress toward goals • Planning skills: Determine strategies to move projects forward; create and implement action plans and evaluate results • Problem-solving skills: Assess problem situations to identify causes, gather and process relevant information, develop possible solutions and make recommendations to resolve • Change orientation: Adapt to change effectively • Demonstrates leading by example and instills a calm, organized approach in all situations 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 of $98,000 - $132,000.00 along with eligibility to earn an annual bonus. Actual pay rate 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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