Windows Server Upgrade Engineer (VMware)

TL;DR

Windows Server Upgrade Engineer (VMware): Performing in-place upgrades of Windows Server systems from 2016 to 2019/2022 within a VMware-based environment with an accent on system stability and application compatibility. Focus on remediating upgrade blockers, validating server health, and executing rollback planning in production environments.

Location: Tampa, FL

Salary: $60/hr

Company

hirify.global is a staffing agency providing technical talent for enterprise infrastructure modernization initiatives.

What you will do

• Perform in-place upgrades of Windows Server 2016 to versions 2019 and 2022.
• Assess and remediate upgrade blockers, including deprecated roles, drivers, and legacy applications.
• Manage VMware snapshots and verify virtual hardware compatibility, disk space, and resource requirements.
• Support and validate core Windows Server roles including Active Directory, DNS, DHCP, and IIS.
• Coordinate maintenance windows and adhere to enterprise change management procedures.
• Document detailed upgrade plans, validation steps, and rollback procedures.

Requirements

• Location: Must be based in or able to work onsite in Tampa, FL
• 2-4+ years of experience in Windows Server administration or infrastructure support.
• Hands-on experience with Windows Server environment upgrades and VMware vSphere/ESXi.
• Proficiency with Active Directory, DNS, DHCP, and IIS.
• Familiarity with PowerShell and standard Windows administration tools.
• Experience operating within enterprise change management frameworks.

Nice to have

• Experience supporting SQL Server environments during OS upgrades.
• Knowledge of Windows Server licensing and upgrade compatibility.
• Experience with enterprise backup and recovery solutions.
• Understanding of security baseline changes between Windows Server versions.