Sr. Windows Engineer

The Judge Group; Chicago (IL); On-site; USD 80,000 - 110,000; Full time

Job summary

A prominent staffing firm is seeking an experienced Windows Systems Administrator to provide advanced operational support for their enterprise-scale environment. The role involves troubleshooting server issues, maintaining system stability, and collaborating with cross-functional teams. Ideal candidates should have over five years of experience with Windows Server and demonstrate strong technical and problem-solving skills. Opportunities exist for growth and development within a fast-paced environment.

Qualifications

• 5+ years of experience performing installation, administration, operations, and maintenance of Windows Server systems.
• Proficiency with PowerShell commands and scripting.
• Experience managing VMware environments.

Responsibilities

• Administer and support Windows Server 2016/2019/2022 systems.
• Perform advanced troubleshooting for Windows Server OS.
• Participate in OS patching cycles and system updates.

Skills

Communication skills

Analytical skills

Problem-solving skills

Collaboration

Education

5+ years of experience with Windows Server

Tools

PowerShell

VMware

SCCM

Job description

We are seeking an experienced Windows Systems Administrator to provide advanced operational support for an enterprise‑scale environment running Windows Server 2016, 2019, and 2022. In this role, you will troubleshoot complex server issues, support system stability, and collaborate with cross‑functional teams to maintain a secure and compliant infrastructure.

Responsibilities

• Administer and support Windows Server 2016/2019/2022 systems in a highly available enterprise environment.
• Perform advanced troubleshooting for Windows Server OS and third‑party application issues, including break/fix support.
• Diagnose hardware and software problems, apply corrective actions, and coordinate with internal teams or external vendors as needed.
• Participate in OS patching cycles, system updates, and vulnerability remediation activities.
• Follow established change‑management processes to ensure system reliability and compliance.
• Ensure adherence to all audit, regulatory, and compliance requirements.
• Assist with server OS migration initiatives (experience in this area is a plus).
• Contribute to additional infrastructure or operational tasks as assigned.

Minimum Qualifications

• Strong communication, analytical, and problem‑solving skills.
• Ability to collaborate effectively with technical teams, stakeholders, and external partners.
• Comfortable working in fast‑paced environments with time‑sensitive deadlines.
• Experience working with distributed teams across multiple locations.

Technical Qualifications

• Extensive hands‑on administration experience with Windows Server 2016/2019/2022.
• Proficiency with PowerShell commands and scripting.
• Experience managing VMware environments and administering virtualized Windows servers.
• Working knowledge of NAS, SAN, and core networking concepts.
• Active Directory administration expertise.
• Experience deploying software via SCCM or comparable tools (preferred).
• Exposure to vulnerability remediation processes (preferred).

Education & Experience

• 5+ years of experience performing installation, administration, operations, and maintenance of Windows Server systems—both physical and virtual—in an enterprise environment.