Desktop Support Jobs in Chicago, IL (NOW HIRING)

Connection Services has a fantastic opportunity for a Desktop Support Specialist to join a dynamic and professional corporate environment in Chicago, IL. This is an excellent opportunity to work for a leading Value-Added Reseller (VAR) that offers outstanding benefits, including three weeks of paid time off, tuition reimbursement, comprehensive medical, dental, and vision coverage, a 401(k) plan, and exceptional opportunities for career growth and advancement.

This role offers a balanced mix of Help Desk Support (50%) and Desktop Support (50%), making it ideal for a customer-focused IT professional who enjoys both remote troubleshooting and hands-on technical support. The successful candidate will possess strong communication skills, exceptional attention to detail, and the ability to work independently while delivering a high level of service to end users in a corporate setting.

Professional Environment

• Business professional attire is required (slacks, button-down shirt, or equivalent business casual attire).
• Experience supporting users in a corporate or financial services environment is highly desirable.

This will be 100% onsite. Hours are M-F, 8am-5pm. Offering hourly rate is $27-$28.50/hr.

What We Do

We calm the confusion of IT by guiding the connection between people and technology. If a customer is looking for a better way to manage their warehouse inventory, equip their workforce, or secure their data, we make it happen. All it takes is finding the right combination of tech hardware, software, cloud solutions, and support services. That's what we do. We're the IT Department's IT Department.

Who We Are

Our team is made stronger by a multitude of backgrounds, experiences, and perspectives. It's what makes Connection unique-what drives us to innovate and create technology solutions that stand apart from the crowd. We'd love for you to be a part of that fabric, to share your ideas and experiences with a team that thrives on fresh thinking, creativity, and helping others.

Why You Should Join Us

You'll find supportive teammates and a rewarding career at Connection-plus great benefits. We take pride in supporting employees with a total rewards package that provides financial, emotional, and physical resources for you and your family.  Our compensation, 401k plans, medical insurance, and other benefits are progressive and competitive.  We value the importance of our employees' emotional wellbeing. To support employees, we provide free therapy visits, mental health coaching and tools, and meditation resources. You'll also enjoy a generous paid time off package that includes not only vacation and sick time, but also Wellness and Volunteer Time Off days. 

Applicants must be authorized to work for any employer in the U.S. We are unable to sponsor or take over sponsorship of an employment visa at this time.

• Serve as the first point of contact for end-user technical support requests via phone, email, and ticketing systems.
• Log, track, prioritize, and manage support tickets while ensuring timely resolution and communication with users.
• Perform initial troubleshooting and diagnosis of hardware, software, operating system, network connectivity, and application-related issues.
• Escalate unresolved incidents to the appropriate support teams and coordinate follow-up activities through resolution.
• Provide regular updates to end users regarding ticket status and expected resolution timelines.
• Process new hire, employee termination, and workstation move requests, ensuring all required systems and access are provisioned appropriately.
• Create, modify, and maintain Active Directory user accounts, profiles, and permissions.
• Coordinate with third-party vendors when necessary and maintain accurate documentation of support activities.
• Install, configure, troubleshoot, and repair desktop and laptop hardware, peripherals, and related equipment.
• Deploy and connect workstations to corporate networks and business systems.
• Perform workstation setup, equipment relocation, software installations, and desktop imaging activities.
• Support data migration efforts and user onboarding initiatives.
• Maintain and manage loaner laptop inventory and related asset tracking processes.
• Assist with Help Desk coverage and support team initiatives as needed.
• Document technical issues, resolutions, and support procedures to improve service delivery.
• Perform additional duties and projects as assigned by management.

• Experience providing Help Desk and/or Desktop Support in a corporate environment.
• Strong customer service skills with a commitment to delivering an exceptional end-user experience.
• Excellent verbal and written communication skills.
• Strong organizational skills with the ability to manage multiple priorities in a fast-paced environment.
• Experience troubleshooting Windows-based desktops, laptops, printers, and common business applications.
• Familiarity with Active Directory user administration.
• Ability to work independently with minimal supervision while maintaining a high level of accuracy and professionalism.
• Strong sense of urgency and responsiveness when addressing user issues and business-critical incidents.

• Experience supporting users within a financial services or corporate enterprise environment.
• Knowledge of desktop imaging, hardware deployment, and software packaging.
• Experience with ticketing systems and IT service management processes.
• Industry certifications such as CompTIA A+, Network+, Microsoft certifications, or similar are a plus.

If you are a customer-focused IT professional who enjoys solving technical challenges, supporting end users, and working in a professional corporate environment, we encourage you to apply.