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Desktop Technician

Wintrust · Rosemont, IL · $42,000–$55,000 a year · Full time

Posted Sep 25, 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 a time you explained a technical fix to someone who wasn't technical.

What they are checking: Whether they can communicate clearly and patiently with everyday users.

How do you stay current with new tools and Windows updates?

What they are checking: Whether they keep learning, since desktop support changes constantly.

What would you do

A branch manager says their teller computer is down and customers are waiting. What do you do?

What they are checking: Whether they understand business impact and act fast while keeping the user calm.

A user asks you to install software that isn't on the approved list. How do you respond?

What they are checking: Whether they follow security policy at a bank, even when a user pushes back.

A user reports a suspicious email with a link. What do you do?

What they are checking: Whether they know to treat it as a possible security incident and escalate it properly.

About the work

Walk me through how you'd troubleshoot a laptop that won't connect to the network.

What they are checking: Whether they work through problems in a logical order instead of guessing.

How have you deployed and imaged new computers for users?

What they are checking: Whether they have hands-on experience with imaging and setup tools used at scale.

What experience do you have with Active Directory, like resetting passwords or managing accounts?

What they are checking: Whether they can handle common account tasks securely and correctly.

How do you keep track of tickets and make sure nothing falls through the cracks?

What they are checking: Whether they use a ticketing system well and follow up until issues are closed.

How do you handle printers, scanners and other devices that branches rely on?

What they are checking: Whether they can support the hardware that daily banking work depends on.

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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? • We hold ourselves accountable to high standards, share wins, operate ethically, and have fun Position Summary The Desktop Technician provides a single point of contact for end-users to receive support and maintenance within the organization’s desktop computing environment. This includes installing, diagnosing, repairing, maintaining, configuring and upgrading all PC hardware, software, and equipment to ensure optimal workstation performance. Troubleshoots problem areas (in person, by telephone, or via e-mail) in a timely and accurate fashion, and provides end-user assistance where required. Responsibilities also include various vendor management related and project management activities. What you’ll do • Manages incidents and service requests queue and resolves daily hardware and software service and support requests. Adheres to established service level agreements. Thoroughly documents work performed in ticketing system. • Installs, configures, troubleshoots, and repairs Windows and Macintosh desktop and laptop computer systems, peripheral equipment and mobile devices. • Follows process documentation and checklists to ensure standardization of work. Proactively recommends documentation changes. • Installs, manages and troubleshoots Microsoft and Macintosh desktop OS systems, as well as, Android and iOS mobile platforms. Completes project tasks as assigned. Meets project dates. Schedules installations/upgrades and provides system maintenance in accordance with IT procedures. Works on site specific department projects and/or sub-projects. Identify opportunities to automate operational processes across the desktop environment • Assists System Engineers as they coordinate, test, and implement enhancements or new releases of Operating System and application packages. • Wintech Express (or other walk-in service areas) - Deploys, troubleshoots and resolves end user hardware and application issues. Customers can walk-in or make a service appointment. • Position requires travel to support Wintrust Corporate or Chicago-area satellite campuses (e.g. 9700, 9701, 9801, FIRST Northbrook, Tricom and 231 LaSalle). Occasional travel to other locations (e.g. banking, mortgage, WAF, WSF, etc.) with some air travel (Domestic/International). Qualifications • 0-3 years Desktop Support, Field Support or related work experience • Familiarity with TCP/IP, DHCP, DNS, LDAP. Solid understanding and experience with LAN/WAN/Internet environments (TCP/IP knowledge -- IP addresses, subnet masks, default gateway…etc.). Working knowledge of Windows Server 2016/2012r2 operating systems and Active Directory in a global enterprise environment • Experience with and understanding of Active Directory and Local Group Policy design and have working proficiency of Forests, Domains, Trusts. Knowledge of or proficiency with handheld wireless devices. Basic understanding of Windows PKI, Certificates • Excellent customer service skills - ability to clearly articulate technical issues and solutions to non-technical users, provide progress updates and complete tasks in a timely manner. • Provide after-hours support for service escalations when required 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 $42,000-$55,000, 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-JB1 #LI-Onsite 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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