Jobs › Wintrust

Advanced IT Asset Manager

Wintrust · Rosemont, IL · $71,000–$92,000 a year · Full time

Posted Aug 18, 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

Tell me about money you saved an employer through asset management, and how you proved it was real.

What they are checking: Quantified impact, and skepticism about their own savings claims.

This is onsite in Rosemont five days a week, reporting to a Senior IT Asset Manager, across a bank running sixteen charters. What would you want to know about the current state of the asset data before you started?

What they are checking: That they read the working conditions and would ask what they are inheriting.

What would you do

A publisher audit arrives. What do you want to have in place before that letter ever lands?

What they are checking: Whether they run the function for audit readiness or react to it.

Discovery says a product is installed on more machines than you have licenses for. Walk me through what you do first.

What they are checking: Investigation before panic — bad data is as likely as a real compliance gap.

You would work with software product owners to keep models approved for use in the environment. How do you handle a team that has already bought something outside the process?

What they are checking: Enforcing governance after the fact, which happens constantly in this role.

How do you work with contract management and purchasing so that maintenance start and end dates never surprise you?

What they are checking: Building a process across teams that do not report to them.

About the work

This role is built around the ServiceNow Software Asset Management Pro module, or equivalents like Flexera or Snow Software. Walk me through how you reconcile entitlement data against discovered installs.

What they are checking: Hands-on reconciliation knowledge, which is the technical heart of the job.

How do you read a software license agreement to work out what the organization is actually entitled to?

What they are checking: Comfort with license terms — perpetual, subscription, seat versus core — rather than just tooling.

Part of this is verifying software has actually been removed when it is retired. Why does disposal matter, and how do you confirm it?

What they are checking: Understanding that reclaiming licenses and meeting regulatory requirements both depend on the end of the lifecycle.

Software as a service licensing behaves differently from perpetual licensing. How does that change what you track?

What they are checking: Whether their practice has kept up with how software is actually bought now.

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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 IT Software Asset Manager is responsible for overseeing the process of acquiring, organizing, maintaining, and disposing of software assets. Additionally, the Software Asset Manager performs regular audits to verify the accuracy of inventory and compliance with software licensing agreements. They analyze software usage data to identify opportunities for cost savings. The Software Asset Manager works closely with designated software model product owners to ensure that software models are approved for use in the environment and have all the proper attributes in the SAM Pro module in ServiceNow. In summary, the software asset manager is a key player, helping to ensure that software assets are effectively managed, effectively utilized, and in compliance with legal and regulatory requirements. Works other projects and tasks as directed by the Sr IT Asset Manager. This position will sit onsite at our Rosemont office location 5 days per week and will report to the Sr. IT Asset Manager. What You’ll Do • Works independently with little supervision, or with a team that supports SAM functions • Subject Matter Expert for ServiceNow Sam Pro Module or other tools that perform same functions (such as Flexera, or SNOW Software) • Ability to recognize, enter and maintain Software License entitlement data, within a Software Model, and reconcile with Software discovered model data • Works with various departments and Software product owners within the enterprise to identify and maintain the software life cycle • Collaborate with contract management and purchasing teams to record properly license agreements and entitlements, and software maintenance start and end dates • Be able to identify and research software license types including SaaS, perpetual, and Freeware, etc. should be able to read and understand SLA’s (Software License Agreements) • Assists product owners and software publishers to ensure that the organization has the appropriate rights to use software in compliance with applicable laws, regulations, and contractual terms • Manages the organization's software inventory, ensuring that software is organized and tracked effectively, and that licenses and maintenance contracts are up to date • Leads the monitoring efforts for software usage to ensure compliance with license agreements and to identify any potential licensing issues • Ensures that software has been disposed properly in accordance with legal and regulatory requirements, including monitoring the system to identify the removal of software from devices that are no longer in use • Understand the Wintrust Software policy and Developing policies and procedures: The Software Asset Manager is responsible for developing and implementing policies and procedures related to the acquisition, organization, and disposal of software assets, and for ensuring that these policies and procedures are followed by all employees in the organization. • Provides reporting and data analysis to Sr IT Asset Manager and other Senior leadership. • Act as a backup to the IT Asset Management Specialist and assist with physical inventory. Qualifications • Bachelor’s degree or equivalent in a business and/or finance related field and a minimum of five (5) years’ related experience is required • 6+ years of Software Asset Management (SAM) experience • 2+ years of Hardware Asset Management (HAM) experience • Hands-on Service Now experience, specifically with SAM Pro module (or equivalent: Flexera, SNOW Software) • Ability to read, interpret, and explain Software License Agreements (SLAs) and EULAs (End User License Agreements) • Ability to identify software license types (SaaS, perpetual, freeware, etc.) • Excellent communication skills, ability to present to and influence senior leadership • Knowledge and proficiency in analytics, automation, and advanced software skills in the use of asset tracking applications • Flexibility to adapt and embrace change in the use of technology with a desire to learn new IT Asset Management skills • Excellent interpersonal and analytical skills, ability to communicate, organization, time management and innovative problem-solving skills are also required for this deadline-oriented position • Knowledge and experience with finance concepts and advanced use of spreadsheets including PivotTables, and VLOOKUP • Demonstrated ability to manage competing priorities and stakeholder expectations • Willingness to travel up to 5% regionally 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 $71,000.00 - $92,000.00, 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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