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Senior Application Specialist/Developer – Payroll

Wintrust Financial

This is a Contract position in Menomonee Falls, WI posted November 29, 2023.

Wintrust is a financial holding company with approximately $50 billion assets under management and traded on the NASDAQ:WTFC. Built on the “HAVE IT ALL” model, Wintrust offers sophisticated technology and resources of a large bank while focusing on providing service-based community banking to each and every customer. Wintrust operates fifteen community bank subsidiaries with over 170 banking locations in the greater Chicago and southern Wisconsin market areas. Additionally, Wintrust operates various non-bank business units including commercial and life insurance premium financing, short-term accounts receivable financing, out-sourced administrative services, mortgage origination and purchase, wealth management services and qualified intermediary services for tax-deferred exchanges.

Why join us?

  • An award-winning culture! We are rated a Top Workplace by the Chicago Tribune (past 9 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 Senior Application Specialist/Developer 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, 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.

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

  • Participate on cross-functional teams to support and define business and technical requirements, operational processes, application strategy, design and administer application software configuration and project/product implementation to meet business process design and application requirements

  • Write and utilize light-weight scripting, software enhancements, reporting, data integration and file formatting utilities/configurations in support of applications and customer specifications

  • Support corporate compliance, regulatory and both internal and external audit examinations and reviews

  • Function as Technical Application Owner for multiple applications within the business domain and provide Tier 2 application level support and troubleshooting, escalation and complex problem solving

  • Understand the interdependencies of systems and data across their business line to identify and analyze impacts as applications and systems are integrated, changed/upgraded and retired

  • Provide leadership, mentoring and training implementing best practices, which may include management of a team or other Application Specialists and must be willing to provide support 24x7x365


  • B.S, B.A. in Computer Science or Business preferred

  • 7-10 years of relevant experience with an emphasis on applications implementation, testing, maintenance, configuration, customization, and support

  • 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.

  • Experience building complex workflows and business process maps required

  • Advanced level experience in the following technologies or similar a plus:

    • Payroll processing systems and ERP platforms, especially Lawson, and ancillary systems such as BSI Tax Factory and Bottomline Transform

    • Proficiency in one or more database system (SQL Server, Oracle, MySQL, etc.)

    • Java and other development languages and technologies, familiarity with COBOL would be ideal

    • SQL Server (SSIS, SSMS, SSRS, and SSAS) to support reporting and integration

    • Crystal Reports for additional reporting

    • Microsoft technologies (SQL, Azure, Office 365, .NET)

    • Application Programming Interfaces (API) and micro services technologies

    • Representational state transfer (REST) architecture

    • Service Oriented Architecture (SOA)

    • Salesforce

    • ServiceNow

    • Mulesoft middleware

    • PowerShell or other scripting technologies


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


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 be Chicago’s Bank® and Wisconsin’s Bank®, we need to reflect that diversity both in all the communities we serve, the people we employ, the organizations we work with, and our banking and lending practices. 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, national origin, sex, sexual orientation, gender identity and expressions, genetic information, marital status, age, disability, or status as a covered veteran or any other characteristic protected by law.