It Support Specialist

We are seeking an experienced IT Support Specialist to provide high-touch technical support at a corporate headquarters environment in downtown Chicago. This position is ideal for someone who thrives in a face-to-face support role and has strong experience with JAMF, Active Directory, Microsoft 365 administration, and executive support.

You will be the go-to resource for employees and leadership, delivering white-glove support while managing endpoint administration, user access, device deployments, and enterprise collaboration technologies.

This is a highly visible role where communication skills, professionalism, and technical expertise are equally important.

Top Skills Required

1. Endpoint Management

• JAMF administration
• Device deployment and provisioning
• macOS and Windows support
• Mobile device management (MDM)
• Endpoint compliance and lifecycle management

2. Active Directory & Access Management

• User provisioning and deprovisioning
• Group and permission management
• Password resets and account troubleshooting
• MFA and authentication support
• Identity and access administration

3. Microsoft 365 Administration

• Exchange Online
• Microsoft Teams
• OneDrive
• SharePoint Online
• Licensing administration
• Advanced end-user troubleshooting

4. Executive Support

• White-glove support for executives and leadership teams
• Conference room and AV support
• VIP troubleshooting and technology consultations
• Event and meeting technology support

Position Overview

The IT Support Specialist serves as a member of the corporate support team, providing advanced desktop, endpoint, and infrastructure support to employees and executive leadership.

This individual will manage the complete endpoint lifecycle, administer Microsoft 365 services, maintain Active Directory access, and provide hands-on support at headquarters. The role combines technical troubleshooting, administration, executive support, and onsite technology operations.

Key Responsibilities

• Provide Tier 2 desktop and technical support for complex escalations
• Administer and support JAMF-managed Mac devices and Windows endpoints
• Manage device imaging, deployment, configuration, and lifecycle management
• Administer Active Directory users, groups, permissions, and access requests
• Support Microsoft 365 services including Exchange, Teams, OneDrive, and SharePoint
• Perform user onboarding, offboarding, and account provisioning activities
• Troubleshoot authentication, access, MFA, and account-related issues
• Support executive leadership with white-glove IT services
• Maintain conference rooms, collaboration technologies, and AV equipment
• Support town halls, leadership meetings, all-hands events, and corporate presentations
• Perform laptop refreshes, upgrades, migrations, and data transfers
• Provide walk-up desk support for onsite employees
• Coordinate mobile device deployments, upgrades, and returns
• Create and maintain technical documentation and knowledge base articles
• Partner with infrastructure, security, and global IT teams on strategic initiatives

Required Qualifications

• 3+ years of desktop support, executive support, or IT support experience
• Hands-on JAMF administration experience
• Strong Active Directory administration experience
• Experience managing Microsoft 365 environments
• Experience supporting both Windows and macOS systems
• Strong troubleshooting skills across hardware, software, and networking
• Experience supporting executives or VIP users
• Excellent customer service and communication skills
• Ability to resolve issues independently and manage competing priorities

Preferred Qualifications

• Experience with Microsoft Intune and Windows Autopilot
• Experience with Entra ID (Azure AD) and Identity Access Management
• Experience supporting conference room technologies and AV systems
• Understanding of endpoint security and compliance best practices
• ITIL-based service management experience
• JAMF, Microsoft 365, Azure, or ITIL certifications

Ideal Backgrounds

• IT Support Specialist
• Executive Support Technician
• Desktop Support Analyst
• Endpoint Management Administrator
• JAMF Administrator
• Systems Support Analyst
• Technical Support Engineer
• Corporate IT Support Specialist
• Desktop Engineer
• Mac Support Engineer

Why Apply?

• Work directly at a corporate headquarters environment
• High visibility supporting executive leadership and key stakeholders
• Exposure to modern endpoint management technologies
• Opportunity to own JAMF administration and device lifecycle processes
• Blend of Microsoft 365 administration, access management, endpoint engineering, and executive support
• Collaborative technology environment with exposure to enterprise-scale IT operations

This role is best suited for someone who enjoys being hands-on, supporting users in person, managing endpoints through JAMF, administering Microsoft 365 and Active Directory, and delivering a high-end support experience for executive leadership and corporate employees.

This is a Contract position based out of Chicago, IL.

The pay range for this position is $25.00 - $30.00/hr.

Individual compensation offered for this position within this range will depend on many factors, including qualifications, skills, relevant experience, job knowledge, geographic location, internal equity, and other pertinent job-related factors.

Eligibility requirements apply to some benefits and may depend on your job classification and length of employment. Benefits are subject to change and may be subject to specific elections, plan, or program terms. If eligible, the benefits available for this temporary role may include the following: Medical, dental & vision Critical Illness, Accident, and Hospital 401(k) Retirement Plan Pre-tax and Roth post-tax contributions available Life Insurance (Voluntary Life & AD&D for the employee and dependents) Short and long-term disability Health Spending Account (HSA) Transportation benefits Employee Assistance Program Time Off/Leave (PTO, Vacation or Sick Leave)

This is a Contract position based out of Chicago, IL.

This position is anticipated to close on Oct 23, 2026.

This is a hybrid position in Chicago,IL.

About TEKsystems

We're partners in transformation. We help clients activate ideas and solutions to take advantage of a new world of opportunity. We are a team of 80,000 strong, working with over 6,000 clients, including 80% of the Fortune 500, across North America, Europe and Asia. As an industry leader in Full-Stack Technology Services, Talent Services, and real-world application, we work with progressive leaders to drive change. That's the power of true partnership. TEKsystems is an Allegis Group company.

The company is an equal opportunity employer and will consider all applications without regards to race, sex, age, color, religion, national origin, veteran status, disability, sexual orientation, gender identity, genetic information or any characteristic protected by law.

About TEKsystems and TEKsystems Global Services

Were a leading provider of business and technology services. We accelerate business transformation for our customers. Our expertise in strategy, design, execution and operations unlocks business value through a range of solutions. Were a team of 80,000 strong, working with over 6,000 customers, including 80% of the Fortune 500 across North America, Europe and Asia, who partner with us for our scale, full-stack capabilities and speed. Were strategic thinkers, hands-on collaborators, helping customers capitalize on change and master the momentum of technology. Were building tomorrow by delivering business outcomes and making positive impacts in our global communities. TEKsystems and TEKsystems Global Services are Allegis Group companies. Learn more at TEKsystems.com.

The company is an equal opportunity employer and will consider all applications without regard to race, sex, age, color, religion, national origin, veteran status, disability, sexual orientation, gender identity, genetic information or any characteristic protected by law.

San Francisco Fair Chance Ordinance: Pursuant to the San Francisco Fair Chance Ordinance, for all positions located in the city and county of San Francisco, we will consider for employment qualified applicants with arrest and conviction records.

Massachusetts Lie Detector: It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.

Use of Artificial Intelligence (AI): We may use Artificial Intelligence (AI) to support parts of our hiring process, including sourcing, screening, and evaluating candidates. AI helps assess applications and qualifications, but final decisions are made by our hiring team. By applying, you acknowledge and agree that your application may be reviewed using AI tools.