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Salary
$90k – $120k per year
Location
In office (Rosemont)
Seniority
Middle · 3+ years exp
Visa
H-1B filings in 12 months: 26 · green card filings: 11
Employment
Full-Time

Confirmed on the employer's own hiring board on Oct 26, 2026. First seen by Alion on Oct 23, 2026. Wintrust Financial scores B on the Alion truth index.

Overview
Company
Impact
Profile match
Wintrust Financial is a bank holding company headquartered in Rosemont, Illinois, and founded in 1991. The company operates a group of separately branded community banks across the Chicago area and southern Wisconsin, alongside specialty businesses in commercial lending, insurance premium finance, mortgage origination, and wealth management. It is listed on the Nasdaq and has grown largely by acquiring local banks while keeping their individual names and branch identities.

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 Advanced Application Specialist is a mid-level position and serves as a subject matter contributor across various debit card technology and other payment systems. 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 acquisition and conversion activities related to their business domains.

What You’ll Do

  • Support the enterprise change management and software development lifecycle (SDLC) process including providing testing, defect management, peer review, and release management ensuring appropriate segregation of duties

· Write and maintain system documentation, process maps, test scripts, use cases, user stories, root cause analysis, and high level integration and data flows

· Participate on cross-functional teams to support and define business and technical requirements, operational processes, application strategy and project/product implementation.

· Author complex system reports and data integration/migration templates

· Write and utilize light-weight scripting and file formatting utilities/configurations in support of applications and customer specifications

· Design and administer application software configuration to meet the business process design and application requirements

· Support complex acquisition and conversion teams to ensure acquired entities data and/or systems are accurately migrated over to the new environments

Qualifications

  • Bachelor’s degree preferred or equivalent experience plus 3-5 years working in a banking or financial services environment with special emphasis on applications implementation, testing, maintenance, configuration, and support
  • Advanced understanding of data at both a functional and technical level in order to troubleshoot and identify potential issues
  • Advanced understanding of how to troubleshoot application/system performance
  • Working knowledge and understanding of hardware and systems software technologies, network infrastructure, and understands issues and details of integrating diverse technology to deliver scalable, robust, and high-performance solutions
  • Ability to analyze, learn, and apply rapidly changing technologies, and apply them as part of integrated solutions to business requirements

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 $90,000.00 - $120,000.00, 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.

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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