Sr. Windows Engineer
Job in
Chicago, Cook County, Illinois, 60290, USA
Listed on 2026-01-29
Listing for:
The Judge Group
Full Time
position Listed on 2026-01-29
Job specializations:
-
Engineering
Job Description & How to Apply Below
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 Power Shell 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.
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