Technical Support Analyst

Addison Group; Chicago (IL); On-site; USD 29,000 - 34,000; Full time

Benefits offered by this job

Medical insurance

Dental insurance

Vision insurance

401(k)

Job summary

Addison Group is seeking a Technical Support Analyst for onsite support at a Chicago-based education and healthcare organization. The role covers Level I/II troubleshooting, Active Directory, Microsoft 365, Citrix, VPN and fielding user inquiries across academic and clinical environments.

You'll manage imaging, WSUS/WDS deployments, patching, and device provisioning for onsite staff and students. This 6-month contract-to-hire position requires strong customer service, documentation, and the

Qualifications

• 1-3+ years of Help Desk, Desktop Support, Technical Support, or End User Support experience.
• Active Directory administration including user and computer account management.
• Experience supporting Microsoft 365 / Office 365.
• Experience troubleshooting Windows desktop environments.
• Understanding of Microsoft Entra ID and Group Policy.
• Imaging and deployment experience.
• Experience with WDS, WSUS, or deployment/patching technologies.
• Experience supporting Citrix and VPN environments.
• Experience with remote-support tools such as Dameware, Remote Desktop, VNC.
• Experience troubleshooting printers (local & network).
• Experience supporting mobile devices.
• Basic networking and switch troubleshooting.
• Experience working in an IT ticketing system.
• Ability to independently perform Level I & Level II troubleshooting.
• Strong problem-solving and communication skills.
• Ability to work independently in fast-paced environment.
• 100% onsite in Chicago; Associate’s degree or higher.

Responsibilities

• Provide onsite, phone, and remote technical support to faculty, staff, and students.
• Troubleshoot hardware, software, applications, accounts, printers, and connectivity.
• Administer user and computer accounts in Active Directory.
• Support Microsoft 365 / Office 365 incl. provisioning & troubleshooting.
• Support identity issues involving Active Directory and Microsoft Entra ID.
• Maintain Group Policy and related workstation issues.
• Create and deploy workstation images using WDS and related tools.
• Assist with Windows patching and WSUS.
• Configure desktops and laptops for new hires and moves.
• Support Citrix, VPN, and VDI environments.
• Use Dameware, Remote Desktop, and VNC for remote support.
• Troubleshoot printers and mobile devices.
• Perform basic network/switch troubleshooting.
• Support client-side hardware and line-of-business apps.
• Monitor ticketing system and update users.

Skills

Help Desk

Active Directory

Microsoft 365

Windows

Group Policy

Imaging

WDS

WSUS

Citrix

VPN

VDI

Remote Support

Printer Support

Mobile Devices

Networking

Ticketing

Onsite Support

Education

Associate’s degree in Information Systems

Equivalent applicable experience/certifications

Bachelor’s degree in Information Systems or related discipline

Tools

Dameware

Remote Desktop

VNC

WDS

WSUS

Citrix

Job description

Industry: Information Technology / Education & Healthcare

Location: Chicago, IL

Work Schedule: Onsite 5x a week

Assignment Type: 6-Month Contract-to-Hire

Pay: $21/hr - $25/hr W2

Start Date: ASAP

About The Opportunity

Our client, a leading educational and healthcare organization in Chicago, is seeking a Technical Support Analyst to provide onsite technical support across its academic and clinical environments.

Key Responsibilities

• Provide onsite, phone, and remote technical support to faculty, staff, and students.
• Perform Level I and Level II troubleshooting across hardware, software, applications, accounts, printers, and connectivity.
• Administer and maintain user and computer accounts within Active Directory.
• Support Microsoft 365 / Office 365, including email account provisioning and troubleshooting.
• Support identity and access-related issues involving Active Directory and Microsoft Entra ID.
• Maintain a working understanding of Group Policy and assist with related workstation and user issues.
• Create, maintain, and deploy workstation images using Windows Deployment Services (WDS) and related imaging technologies.
• Assist with Windows patching and WSUS.
• Configure and deploy desktops and laptops for new hires, replacements, and workstation moves.
• Support Citrix, VPN, VDI, and remote‑access environments.
• Utilize remote‑support technologies such as Dameware, Remote Desktop, and VNC.
• Troubleshoot local and network‑connected printers.
• Provide technical support for mobile and IoT devices.
• Perform basic network and switch troubleshooting.
• Support client‑side hardware, software, and line‑of‑business applications.
• Monitor the ticketing system and proactively communicate status updates to users.
• Gather necessary technical information and thoroughly triage issues before escalating them to Systems, Network, or other specialized teams.
• Assist with employee onboarding, offboarding, relocations, and account changes.
• Test new software releases, patches, and upgrades.
• Maintain accurate hardware and technology asset inventory.
• Provide one‑on‑one technology training to end users.
• Create and maintain technical documentation, procedures, and training materials.
• Participate in small and large IT projects.
• Assist with patch‑management activities and monthly maintenance windows.
• Participate in after‑hours and non‑business‑day support when required.

Required Qualifications

• 1-3+ years of Help Desk, Desktop Support, Technical Support, or End User Support experience.
• Hands‑on Active Directory administration, including user and computer account management.
• Experience supporting Microsoft 365 / Office 365.
• Experience troubleshooting Windows desktop environments.
• Understanding of Microsoft Entra ID and Group Policy.
• Hands‑on desktop imaging and deployment experience.
• Experience with WDS, WSUS, or comparable deployment/patching technologies.
• Experience supporting Citrix and VPN environments.
• Experience with remote‑support tools such as Dameware, Remote Desktop, VNC, or similar technologies.
• Experience troubleshooting local and network‑connected printers.
• Experience supporting mobile devices.
• Basic network‑connectivity and switch troubleshooting skills.
• Experience working within an IT ticketing system.
• Ability to independently perform Level I and appropriate Level II troubleshooting.
• Strong problem‑solving and technical triage skills.
• Excellent customer service and interpersonal skills.
• Strong written and verbal communication.
• Ability to manage multiple priorities while maintaining professionalism in a fast‑paced environment.
• Ability to work independently with minimal supervision.
• Associate’s degree or higher in Information Systems or a related discipline, or equivalent applicable experience/certifications.
• Ability to work 100% onsite in Chicago.

Preferred Qualifications

• Previous healthcare or higher‑education IT support experience.
• Microsoft Certified Professional (MCP), CompTIA A+, or comparable technical certification.
• Bachelor’s degree in Information Systems or a related discipline.
• Experience supporting Virtual Desktop Infrastructure (VDI).
• IoT device support experience.
• Healthcare technology experience.
• Familiarity with HIPAA and healthcare data/security considerations.
• Asset‑management experience.
• Experience developing IT procedures and end‑user training materials.
• Experience supporting environments with multiple physical locations.

What We’re Looking For

This role goes beyond resetting passwords and routing tickets.

The strongest candidate will be someone who can receive an issue, troubleshoot it through Level I/II, identify where the problem exists within the technology stack, and either resolve it or provide a thorough technical handoff before escalation.

We’re particularly interested in candidates who can demonstrate hands‑on experience with:

• Microsoft 365
• Active Directory
• Microsoft Entra ID
• Group Policy
• Windows
• Desktop Imaging
• WDS / WSUS
• Citrix
• VPN
• VDI
• Remote Desktop Support
• Printer Support
• Mobile Device Support
• Basic Networking
• Ticket Management

Experience creating and maintaining desktop images is particularly valuable for this position.

Support Environment

You’ll join a collaborative IT team of approximately 8 professionals supporting both academic and clinical operations.

The environment includes faculty, staff, students, healthcare operations, end‑user devices, business applications, mobile technologies, and multiple physical locations.

Because the organization supports both education and patient‑care environments, strong customer service, professionalism, documentation, and technical troubleshooting are critical.

Work Environment & Physical Requirements

• 100% onsite in Chicago during the contract period
• Must be able to efficiently travel to other local organizational locations when required.
• Candidates must have reliable access to transportation.
• Ability to participate in after‑hours/non‑workday support and scheduled maintenance activities.
• Participation in 24x7 support coverage rotations may be required.
• Ability to lift equipment weighing up to approximately 50 pounds.
• Ability to stand for extended periods when performing onsite support.
• Some work may occur in cooler data‑center environments.

Additional Details

• 6-month contract-to-hire
• Pay $21/hr - $25/hr W2
• ASAP start
• 100% onsite during the contract period
• Two-step interview process:
• Hiring Manager interview
• Final/team interview, including an onsite interview
• Upon a conditional offer of employment, the position requires a background check

Benefits

This position is eligible for medical, dental, vision, and 401(k).

Addison Group is an Equal Opportunity Employer. Addison Group provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, gender, sexual orientation, national origin, age, disability, genetic information, marital status, amnesty, or status as a covered veteran in accordance with applicable federal, state and local laws. Addison Group complies with applicable state and local laws governing non-discrimination in employment in every location in which the company has facilities. Reasonable accommodation is available for qualified individuals with disabilities, upon request.

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