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Windows System Administrator

Remote · USA Full-time New today

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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