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