Job Description

Job Summary:

The Windows Server Upgrade Engineer will be part of a Server Operations team and will support the day-to-day technical operations of a large-scale infrastructure environment consisting of approximately 1,800 physical and virtual servers running on Dell hardware and Hyper-V. This role involves assessing complex technical issues, recommending and implementing solutions, and providing administration and oversight for server hardware and software infrastructure. The ideal candidate is a self-starter who can independently drive tasks to completion and quickly adapt to changing technical demands.

Key Responsibilities:

• Coordinate with application owners to schedule and perform comprehensive Windows Server OS upgrades, including in-place upgrades and new deployments (e.g., 2012 to 2016/2019/2025) within a large-scale Hyper-V environment.
• Perform physical hardware upgrades on Dell R620 servers across multiple sites, using Dell tools such as iDRAC, onboard flash memory, and Dell OpenManage Essentials (OME).
• Develop and utilize automation scripts using PowerShell, Ansible, or similar tools to streamline OS deployments, upgrades, and repetitive operational tasks.
• Work independently, taking direction from managers or team leads to complete server provisioning and support activities.
• Collaborate with team members to provide cross-training on roles and responsibilities.
• Manage day-to-day server operations using standard enterprise tools.
• Respond to and resolve alerts generated by server infrastructure monitoring systems.
• Work closely with application teams to resolve software installation and compatibility issues on managed servers.
• Coordinate with third-party vendors for support, recommendations, and issue resolution.
• Perform initial entry of enterprise server assets into the server asset management database.
• Participate in a 24x7 Windows Server on-call rotation to support critical server emergencies.

Education & Certifications:

• Bachelor’s degree or equivalent experience preferred.
• Microsoft certifications (e.g., MCSE) are a plus but not required.

Experience Requirements:

• 5+ years of experience managing Windows Server OS (2012, 2016, 2019, 2025) in an enterprise Hyper-V / SCVMM environment.
• Expert-level Windows troubleshooting and triage experience.
• Proven experience planning and executing OS upgrades, including in-place upgrades and new deployments.
• Hands-on experience with Dell server hardware (e.g., R620) and remote management tools such as iDRAC and Dell OpenManage Essentials (OME).
• Experience with Microsoft Failover Clustering, host/OS patching, migrations, SCCM, and Azure administration.

Knowledge, Skills, and Abilities:

• Strong scripting and automation skills using PowerShell, Ansible, or similar technologies.
• Excellent planning, organizational, and prioritization skills, with the ability to manage multiple projects simultaneously.
• Experience translating business requirements into IT specifications, including strategy, platform selection, and reference architecture designs.
• Strong interpersonal, collaboration, leadership, facilitation, and conflict-management skills.
• Excellent communication skills, with the ability to clearly explain complex technical concepts to both technical and non-technical audiences.
• Strong commitment to leveraging information technology to positively support organizational and community outcomes.

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