Senior System Administrator

We are seeking an experienced Senior Systems Administrator for a client of ours that is a beloved, Chicago-based restaurant brand to support and maintain a complex, hybrid Microsoft infrastructure environment. This individual will play a key role in ensuring the reliability, efficiency, and performance of critical systems supporting a growing, multi-location organization.

The ideal candidate brings strong hands-on experience across Microsoft Azure, Windows Server, Active Directory, and Microsoft 365, along with the ability to independently troubleshoot complex technical issues. We are looking for someone who is technically strong, adaptable, and comfortable working in a fast-paced environment where system availability and responsive support are essential.

Key Responsibilities

• Administer, maintain, and troubleshoot Microsoft Azure, Windows Server, and Microsoft 365 environments.
• Manage Active Directory, Microsoft Entra ID, Group Policy, DNS, DHCP, and hybrid identity configurations.
• Support Azure infrastructure, including virtual machines, virtual networks, storage, and related cloud services.
• Administer Microsoft 365 services, including Exchange Online, Teams, SharePoint, and Intune/Endpoint Manager.
• Manage and support VMware virtualization environments, including vSphere, ESXi, and vCenter.
• Troubleshoot and resolve escalated infrastructure, system, and end-user issues independently.
• Support infrastructure and connectivity across multiple locations, ensuring system reliability and minimal disruption to operations.
• Assist with system upgrades, migrations, patching, security improvements, and infrastructure projects.
• Monitor system performance, identify potential issues, and proactively recommend improvements.
• Collaborate with internal IT teams and business stakeholders to deliver effective technical solutions.

Required Qualifications

• Strong experience in Microsoft systems administration within a hybrid cloud and on-premises environment.
• Hands-on experience administering and troubleshooting Microsoft Azure infrastructure.
• Strong knowledge of Windows Server, Active Directory, Group Policy, DNS, and DHCP.
• Experience with Microsoft Entra ID (Azure AD), hybrid identity, and Entra Connect.
• Proficiency administering Microsoft 365, including Exchange Online, Teams, and SharePoint.
• Experience with Microsoft Intune / Endpoint Manager.
• Working knowledge of VMware virtualization technologies.
• Demonstrated ability to independently resolve complex technical issues and escalated incidents.
• Experience supporting distributed or multi-site business environments.
• Strong communication, problem-solving, adaptability, and customer-service skills.
• Ability to prioritize competing demands and work effectively both independently and collaboratively.

MMD Services Inc. is an equal opportunity employer. All applicants are considered for all positions without regard to race, religion, color, sex, gender, sexual orientation, pregnancy, age, national origin, ancestry, physical/mental disability, medical condition, military/veteran status, genetic information, marital status, ethnicity, alienage, or any other protected classification, in accordance with applicable federal, state, and local laws.