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Agent guide: [/agents.md](https://www.wearedevelopers.com/agents.md). --- # It Support Specialist - **Company:** TEKSYSTEMS INC. - **Location:** Chicago, IL, United States - **Experience:** Experienced - **Salary:** $52,000.0 - $62,400.0 - **Contract:** Temporary contract - **Skills:** Microsoft Windows, Active Directory, Apple Mac Systems, Microsoft Azure, Microsoft Online Services, Identity and Access Management, Information Technology Operations, Azure Active Directory, Microsoft SharePoint, User Provisioning Software, Microsoft InTune, Information Technology, Deployment Automation, Casper Suite, User Administration - **Published:** October 17, 2026 - **Apply:** https://dejobs.org/x/x/D6FA3CAC388947348B4179D3B666ABB5/job/ ## About the Role 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 Required1. 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, * 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, * 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 ## Description 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, * 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.