Senior Systems Administrator

Housing Authority of Cook County; Chicago (IL); On-site; USD 110,000 - 140,000; Full time

Benefits offered by this job

Healthcare flexible spending account

Employee Assistance Program (EAP)

Paid time off including 14 Holidays

401(k) – Employer contribution of 6%

Job summary

The Senior Systems Administrator at Housing Authority of Cook County oversees the enterprise IT infrastructure, bridging on‑premises and cloud platforms. You will own VMware vSphere, Windows Server architecture, and core identity services, while guiding security governance and operational resilience.

Responsibilities include designing and administering Microsoft 365 workloads, implementing Entra ID, Intune, Purview, and Automating tasks with PowerShell, plus supporting disaster recovery and

Qualifications

• 5+ years hands-on experience administering Microsoft 365 environments including Intune, Entra ID, Exchange Online, SharePoint Online, Teams, and Purview.
• Proven expertise in VMware vSphere/ESXi/vCenter administration and troubleshooting.
• Experience administering Windows Server, AD DS, GPO, DNS, and DHCP.
• Proficient in PowerShell scripting for automation and configuration.
• Familiar with Remote Monitoring & Management (RMM) tools and remote endpoint management.

Responsibilities

• Design, implement, and administer Microsoft 365 services including security baselines and compliance controls.
• Manage VMware virtualization infrastructure, backup, DR, and business continuity strategies.
• Administer Windows Server environments, patching, performance tuning, and core services.
• Develop automation, enforce change management, and maintain thorough system documentation.

Skills

Microsoft 365 Administration

VMware vSphere/ESXi/vCenter

Windows Server Administration

PowerShell scripting

Identity management (Entra ID)

Intune/Autopilot device management

RMM tools experience

Security governance & compliance

Hybrid cloud / on-premise architecture

Education

Bachelor's degree in IT/CS/MIS or related field

Tools

VMware vCenter

Microsoft Purview

Microsoft Entra ID

Microsoft Intune

Job description

The Senior Systems Administrator is a senior-level technical role responsible for the architecture, administration, security governance, and operational resilience of the Housing Authority of Cook County's enterprise IT infrastructure. This position bridges on-premises environments with modern cloud platforms, maintaining direct ownership of VMware vSphere virtualization, Windows Server architecture, core identity services, and enterprise Microsoft 365 cloud workloads.

Essential Duties and Responsibilities

• Microsoft 365 Architecture & Administration: Design, implement, and administer M365 services—including Exchange Online, SharePoint Online, and Teams. Manage identity, authentication, and access via Microsoft Entra ID. Configure security baselines, data governance, and compliance controls through Microsoft Purview. Manage device lifecycles, configuration, and endpoint security utilizing Microsoft Intune and Autopilot.
• VMware Virtualization & Infrastructure: Manage, optimize, and troubleshoot VMware vSphere and ESXi host environments, including virtual machines, resource allocation, virtual networking, and datastore management. Support backup, disaster recovery, and business continuity strategies.
• Windows Server & Core Services: Administer Windows Server environments, including deployment, patching, performance tuning, and troubleshooting. Manage Active Directory Domain Services (AD DS), Group Policy Objects (GPO), DNS, and DHCP. Execute software deployments, script-based configuration, and remote endpoint management using RMM platforms and PowerShell.
• Automation, Governance & Operations: Develop PowerShell scripts to automate routine administrative tasks, deployments, and reporting. Enforce change management protocols, security standards, and system-hardening practices. Maintain comprehensive system documentation, perform root-cause analysis for incidents, and collaborate across teams for hybrid infrastructure initiatives.

Qualifications

Required

• Minimum of 5 years of hands‑on experience administering Microsoft 365 environments, including Intune, Entra ID, Exchange, SharePoint, Teams, and Purview.
• Demonstrated expertise in managing, maintaining, and troubleshooting VMware vSphere, ESXi, and vCenter.
• Proven experience administering Windows Server, Active Directory, GPO, DNS, and DHCP.
• Proficiency in PowerShell scripting for task automation and configuration.
• Experience leveraging Remote Monitoring and Management (RMM) tools.
• Valid driver’s license and dependable transportation for travel to agency locations.

Preferred

• Bachelor's degree in Information Technology, Computer Science, Cybersecurity, Management Information Systems, or a related field.
• Relevant Microsoft Certifications (e.g., M365 Certified: Enterprise Administrator Expert, Identity and Access Administrator Associate).
• VMware Certified Professional (VCP-DCV).
• Industry-standard certifications such as CompTIA Security+, Network+, or ITIL Foundation.

• Healthcare flexible spending account
• Employee Assistance Program (EAP)
• Paid time off including 14 Holidays
• 401(k) – Employer contribution of 6%

This job description is subject to change and in no manner states or implies that these are the only duties and responsibilities to be performed. The qualifications listed above are guidelines, other combinations of education and experience that could provide the necessary knowledge, skills, and abilities to perform the job will be considered.