Windows System Administrator

Remote Full-time
Position Summary

We are seeking a Systems Administrator to join our Infrastructure team in a contract-to-hire capacity. This individual will support a large enterprise server environment consisting primarily of Windows servers with a smaller Red Hat Linux footprint. The role will be responsible for server patching, operating system upgrades, infrastructure support, ticket resolution, and participation in maintenance activities and on-call support.

This position follows a unique Sunday–Thursday schedule to support planned maintenance windows and infrastructure initiatives while collaborating closely with the engineering team throughout the week.

Schedule
• Sunday: 10:00 AM – 7:00 PM EST
• Monday – Thursday: 8:00 AM – 5:00 PM EST
• Remote opportunity
• Participation in an evening on-call rotation may be required

Key Responsibilities
• Perform scheduled server maintenance, patching, and remediation activities during designated Sunday maintenance windows.
• Execute operating system upgrade projects, including migration efforts from Windows Server 2016 to Windows Server 2022.
• Administer and support a large-scale server environment of approximately 2,000+ servers.
• Manage and support Windows Server infrastructure (approximately 95% of the environment).
• Provide support for Red Hat Linux servers within the enterprise environment.
• Investigate, troubleshoot, and resolve infrastructure-related tickets and incidents.
• Deploy security patches and ensure compliance with organizational security standards.
• Collaborate with infrastructure and operations teams to plan, coordinate, and execute maintenance activities.
• Utilize monitoring, security, and remote access technologies, including Zscaler.
• Document procedures, configurations, and maintenance activities.
• Participate in after-hours support and on-call rotation as needed.

Required Qualifications
• 4+ years of Systems Administration or Infrastructure Support experience.
• Strong experience administering Windows Server environments.
• Experience performing server patching, maintenance, and operating system upgrades.
• Knowledge of Active Directory, Group Policy, DNS, DHCP, and core Microsoft infrastructure technologies.
• Experience troubleshooting server, operating system, and infrastructure issues.
• Familiarity with enterprise ticketing systems and incident management processes.
• Understanding of security best practices and vulnerability remediation.
• Ability to work independently in a remote environment and manage maintenance activities with minimal supervision.

Preferred Qualifications
• Experience supporting Red Hat Enterprise Linux (RHEL) servers.
• Experience with enterprise-scale server environments.
• Familiarity with Zscaler or similar security platforms.
• Experience participating in infrastructure on-call rotations.
• Exposure to automation and scripting technologies such as PowerShell.
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