Windows System Administrator

Role: System Administrator Location: Remote 6+ Months Contract Role Overview We are seeking a skilled System Administrator with hands-on experience in Windows Server upgrades and migrations, specifically transitioning from Windows Server 2016 to Windows Server 2022. The ideal candidate will play a key role in planning, executing, and supporting enterprise server upgrade initiatives while ensuring minimal downtime and high system performance.

Key Responsibilities

Lead and execute Windows Server upgrade projects from 2016 to 2022 Perform server migration, installation, configuration, and deployment activities Conduct pre-upgrade assessments, compatibility checks, and risk analysis Manage Active Directory, DNS, DHCP, and other core Windows services Coordinate with network, application, and infrastructure teams for seamless migration Perform patching, performance tuning, and system optimization Ensure data integrity, backup validation, and disaster recovery readiness Troubleshoot and resolve server-related issues during and post migration Document configurations, processes, and migration procedures Required Skills & Qualifications 5+ years of experience in Windows System Administration Strong hands-on experience with: Windows Server 2016 & 2022 Server upgrade & migration strategies (in-place / side-by-side) Active Directory, Group Policies, DNS, DHCP Strong SCCM/Intune experience OS imaging (rolling out new OS versions to laptops and VMs) Patch automation and management (create automation for most of our applications in our environment) Device management (Configuration policies, OS updates, etc..) Strong PowerShell scripting knowledge VMware/VDI experience Friendly and helpful and is willing to teach people below them Preferred Skills Experience with large-scale enterprise server migration projects Exposure to cloud environments (Azure/AWS) Understanding of ITIL processes and change management