Windows Server Engineer Migration Validation

Windows Server Engineer Migration Validation

Location - Remote

Work Hours - Will need flexibility to work late hours 10 pm - 2 AM EST

Migration

Role Summary:
Seeking an experienced Windows Server Engineer to support large-scale server migration projects by performing pre- and post-migration validation, ensuring successful cutovers, and developing automation to streamline health checks. The team will be responsible for validating approximately 100 Windows servers per day in a high-volume migration environment.

Key Responsibilities:

• Perform pre-migration validation to confirm server readiness, application dependencies, network connectivity, and baseline system health.
• Execute post-migration validation to verify successful migration and ensure all services, applications, and infrastructure components are functioning as expected.
• Validate that cutover activities are complete, confirming server accessibility, DNS updates, application availability, authentication, scheduled tasks, and service status.
• Develop and maintain PowerShell automation and scripts to perform standardized health validation across large server populations.
• Troubleshoot and resolve validation failures, working closely with migration, application, infrastructure, and operations teams.
• Generate validation reports, document issues, and provide migration signoff based on defined acceptance criteria.
• Support high-volume migration events, validating approximately 100 servers per day while meeting established SLAs.

Required Skills & Experience:

• 10+ years of Windows Server administration experience (Windows Server 2016/2019/2022).
• Strong experience supporting enterprise server migration or data center migration projects.
• Advanced PowerShell scripting skills for automation and health validation.
• Experience validating Windows services, Event Logs, scheduled tasks, IIS (where applicable), DNS, Active Directory, file shares, networking, and application connectivity.
• Strong troubleshooting skills across Windows OS, networking, storage, and authentication.
• Experience working in ITIL-based change and release management environments.
• Ability to prioritize and manage validation activities across large-scale migration waves.

Preferred Qualifications:

• Experience with VMware or Hyper-V environments.
• Familiarity with monitoring tools such as SCOM, SolarWinds, or similar enterprise monitoring platforms.
• Experience with Azure or hybrid cloud migrations.
• Knowledge of automation frameworks, CI/CD pipelines, or infrastructure-as-code tools is a plus.

This role is ideal for an engineer who combines strong Windows infrastructure expertise with automation skills to ensure migration quality, minimize downtime, and efficiently validate large-scale migration events.