IT Support Specialist

Addison Group; Chicago (IL); Hybrid; USD 75,000 - 95,000; Full time

Benefits offered by this job

Medical, dental, vision

401(k)

Health savings account

Transit benefits

EAP

Travel assistance

Fitness center access

Disability & life insurance

Job summary

Addison Group in Chicago is seeking an experienced IT Support Specialist to join its internal technology team in a hybrid role, requiring 2 onsite days per week. The position centers on Windows 11, Microsoft 365, Active Directory, and business applications, with exposure to AI tools like Copilot for productivity and compliance.

You will troubleshoot hardware and software, support remote access, and assist with onboarding, documentation, and user training while delivering high-touch service to

Qualifications

• 4–6+ years of IT support experience.
• Proficiency with Microsoft 365 and Windows 11.
• Experience with Active Directory and business applications.
• Familiarity with AI tools like Copilot.

Responsibilities

• Provide hands-on desktop, application, phone, and remote support.
• Troubleshoot Windows 11, Microsoft 365, Outlook, and AD.
• Support desktops, laptops, mobile devices, and conference tech.
• Assist with VPN, Citrix, and Remote Desktop access.
• Document steps and resolutions in the ticketing system.
• Assist onboarding/offboarding and access provisioning.
• Support AI tools adoption and Copilot.
• Train employees on security practices and productivity tools.

Skills

Microsoft 365

Windows 11

Active Directory

Remote access (VPN)

Customer service

Ticketing systems

AI tools (Copilot)

Education

Bachelor’s or Associate degree in IT

Tools

ServiceNow

SysAid

Citrix

VPN

Remote Desktop

Job description

Role: IT Support Specialist

Industry: Legal / Professional Services

Location: Chicago, IL – Hybrid, 2 days onsite per week

Assignment Type: Direct Hire

Salary: $75,000 – $95,000 / year

Benefits: This role is eligible for medical, dental, vision and 401 k. Along with:

• Complimentary disability, life and AD&DD insurance
• 401(k) plan
• Health savings account
• Paid transportation to and from the office up to $300 per month
• Pre-tax transit and commuter benefits program
• Accident, Critical Illness and Hospital Indemnity insurance
• Complimentary Employee Assistance Program (EAP)
• Travel assistance program
• Complimentary access to onsite fitness center

About The Company

Our client is an established Chicago-based professional services organization seeking an experienced IT Support Specialist to join its internal technology team.

This is an excellent opportunity for an IT support professional who enjoys solving technical problems while working directly with business professionals in a fast-paced, high-touch environment.

This position goes beyond traditional help desk support. The IT Support Specialist will support Windows 11, Microsoft 365, Active Directory, desktop and mobile devices, business applications, remote-access technologies, and emerging AI tools such as Microsoft Copilot and legal-focused generative AI platforms.

The ideal candidate combines strong technical troubleshooting abilities with exceptional customer service and the confidence to support demanding professional users.

Job Description

The IT Support Specialist will provide intermediate-level technical and application support to employees across the organization. You will independently troubleshoot hardware, software, application, access, and connectivity issues while helping users effectively adopt new technologies.

This position will also play a role in the organization's continued adoption of AI-powered productivity tools, providing first-level support and helping users understand how to use approved AI technology safely and effectively.

Key Responsibilities

• Provide hands-on desktop, application, phone, and remote technical support
• Troubleshoot Windows 11, Microsoft 365, Outlook, Teams, and Active Directory
• Support desktops, laptops, mobile devices, peripherals, and conference room technology
• Troubleshoot hardware failures and workstation performance issues
• Support remote-access technologies including VPN, Citrix, and Remote Desktop
• Assist with software installation, configuration, upgrades, and patching
• Provide support for firm-specific SaaS and business applications
• Support applications such as CRM, HRIS, document management, timekeeping, and other enterprise systems
• Assist users with access, functionality, configuration, and troubleshooting of business applications
• Document troubleshooting steps and resolutions within the ticketing system
• Assist with onboarding and offboarding, including account setup, equipment preparation, and access provisioning
• Maintain accurate support, asset, and ticket documentation
• Contribute to IT procedures, runbooks, FAQs, and knowledge-base content
• Assist with workstation imaging and deployment
• Train employees on technology, applications, security practices, and productivity tools
• Provide hands-on support for video conferencing, meetings, and conference room technology
• Identify recurring technical issues and recommend improvements

AI & Copilot Support

This role will also help support the organization's growing use of artificial intelligence and generative AI tools.

Responsibilities may include:

• Provide first-level support for Microsoft Copilot and other approved AI platforms
• Troubleshoot AI tool access, login, and basic functionality issues
• Help users effectively utilize AI for drafting, summarization, research assistance, and workflow efficiency
• Educate users on safe and compliant use of generative AI
• Assist with adoption of legal-focused AI technologies
• Use AI tools to improve ticket documentation, troubleshooting, and root-cause analysis
• Help develop AI-related FAQs, documentation, and best practices
• Identify recurring AI-related support issues and elevate more complex problems when appropriate

Required Qualifications

• 4–6+ years of IT technical support, desktop support, or end-user support experience
• Strong experience supporting Microsoft 365
• Strong Windows 11 troubleshooting experience
• Experience supporting Microsoft Outlook and Teams
• Working knowledge of Active Directory
• Experience supporting business or enterprise applications in addition to traditional desktop support
• Previous exposure to AI tools such as Microsoft Copilot, ChatGPT, or other generative AI platforms
• Experience supporting VPN and remote-access technologies
• Experience working with ticketing systems such as ServiceNow, SysAid, or similar platforms
• Strong hardware, software, and peripheral troubleshooting abilities
• Excellent customer service and communication skills
• Ability to communicate technical concepts to non-technical users
• Ability to independently troubleshoot moderately complex technical issues
• Ability to prioritize multiple requests in a fast-paced environment

Preferred Qualifications

• Previous law firm or legal technology experience
• Experience supporting users within financial services, consulting, accounting, or another professional services environment
• Experience supporting legal-specific applications
• Experience with CRM platforms such as ContactEase
• Experience supporting UKG or similar HRIS applications
• Microsoft Copilot experience
• Exposure to legal-focused generative AI platforms such as Harvey
• Associate's or Bachelor's degree in Information Technology, Computer Science, or a related field
• Microsoft 365 certifications
• CompTIA A+ or equivalent technical certification

What We're Looking For

The strongest candidate will be someone who combines technical troubleshooting with polished, high-touch customer service.

You’ll be supporting professionals who expect responsive and accurate technology support, so the ability to remain composed, communicate confidently, and take ownership of issues is extremely important.

We’re particularly interested in candidates coming from law firms, financial services, consulting, accounting, or other professional services organizations where IT teams directly support demanding business users.

This is also a great opportunity for someone interested in the evolution of AI within the workplace. You don't need to be an AI engineer, but you should have hands‑on exposure to tools such as Microsoft Copilot or similar generative AI platforms and be comfortable helping users adopt new technology.

Interview Process

• 30-minute virtual interview with the CIO
• Onsite interview with four members of management
• Potential final conversation with an attorney

Why Consider This Opportunity?

• Competitive $75K – $100K salary
• Hybrid schedule with only 2 required onsite days per week
• Join a close-knit internal IT team
• Opportunity to work beyond traditional desktop support and gain deeper application experience
• Hands‑on exposure to Microsoft Copilot, generative AI, and emerging legal technology
• Work with Microsoft 365, Active Directory, business applications, remote‑access technology, and enterprise systems
• Opportunity to join an organization investing in modernization and responsible AI adoption

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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