Senior Windows Server Modernization Specialist

We are hiring for a Senior Windows Server Modernization Specialist. The role focuses on enterprise-wide Windows Server modernization, including large-scale in-place upgrades, infrastructure administration, automation, troubleshooting, and production support.
A strong fit will have 5+ years of Windows Server experience with expertise in PowerShell, enterprise upgrades, virtualization, cloud-hosted infrastructure, and change management.

What you bring

• 5+ years of hands-on experience administering and supporting Microsoft Windows Server 2012 and newer environments.
• Strong experience with PowerShell scripting and automation for deployments, validation, reporting, and operational efficiency.
• Proven expertise in Windows Server installation, configuration, upgrades, patching, troubleshooting, recovery, and validation.
• Experience planning and executing large-scale Windows Server upgrade and migration projects.
• Hands-on experience with VMware vSphere, Microsoft Hyper-V, and cloud-hosted Windows infrastructure.
• Strong understanding of enterprise Change Management and governance frameworks.
• Experience supporting maintenance windows, production deployments, releases, and implementation activities.
• Working knowledge of Microsoft SCCM/MECM, VMware SaltStack, Dynatrace, and related infrastructure management tools.
• Experience with ServiceNow and IT Service Management platforms.
• Strong understanding of ITIL Incident, Change, Problem, and Release Management processes.
• Strong analytical, troubleshooting, organizational, and time management skills.
• Excellent verbal and written communication skills with the ability to create technical documentation and work with technical and business stakeholders.

What you'll do

• Lead and execute Windows Server 2016 to Windows Server 2025 in-place upgrade activities across enterprise environments.
• Perform server readiness assessments, compatibility reviews, upgrade planning, implementation, validation, and post-upgrade support.
• Coordinate application testing, validation, and issue remediation following server upgrades.
• Troubleshoot complex operating system, application, and infrastructure issues during upgrade and migration projects.
• Collaborate with application support, infrastructure operations, security, cloud engineering, and project stakeholders.
• Develop and maintain technical documentation, implementation procedures, recovery plans, and operational standards.
• Ensure compliance with enterprise change management, security, and operational governance processes.
• Participate in incident management, production support, maintenance windows, and after-hours implementations.
• Identify opportunities for automation, process improvement, and standardization throughout the server modernization lifecycle.
• Provide technical guidance on upgrade readiness, implementation planning, risk mitigation, and operational support.
• Support enterprise infrastructure environments consisting of thousands of Windows servers across global regions.

Nice to have

• Microsoft certifications such as MCSE, Azure, Windows Server, or equivalent.
• Experience supporting Windows Server 2022 and Windows Server 2025 environments.
• Experience working within highly regulated environments such as banking or financial services.