Windows Server 2016 Upgrade & Build Engineer

Job Description:

Role Overview

This role supports the Windows Server 2016 Retirement Program, ensuring all servers are upgraded or rebuilt to meet compliance and security standards before the January 2027 end-of-life deadline. The resource will work closely with Platform Engineering, Platform Operations, and application owners to execute upgrade workflows across VMware, Nutanix, Azure, and AWS environments, while adhering to corporate standards for automation, monitoring, and security.

Key Responsibilities

• Upgrade Execution
• Perform in-place upgrades and new builds for Windows Server 2016 to supported OS versions.
• Validate upgrade paths and ensure minimal downtime during migrations.
• Automation & Scripting
• Read and understand PowerShell scripts for upgrade automation.
• Execute automation workflows into Azure DevOps pipelines.
• Infrastructure Integration
• Configure servers for compliance with enterprise standards (GPOs, baseline hardening).
• Ensure integration with management tools: BigFix, Splunk, SCOM, CyberArk.
• Security Enablement
• Deploy and validate security agents (CrowdStrike, Morphisec).
• Confirm adherence to CIS benchmarks and internal security posture requirements.
• Documentation & Reporting
• Maintain accurate upgrade logs and configuration documentation.
• Provide status updates and participate in weekly planning/progress meetings.

Required Skills & Experience

• Technical Expertise
• Strong experience with Windows Server administration (2016/2019/2022).
• Familiarity with VMware, Nutanix, and AWS EC2 environments.
• Automation
• Proficiency in PowerShell scripting and Azure DevOps pipeline integration.
• Tools & Platforms
• Experience with BigFix patching, Splunk monitoring, CyberArk credential management, and SCOM.
• Security
• Knowledge of endpoint security tools (CrowdStrike, Morphisec) and compliance frameworks (CIS).
• Soft Skills
• Ability to collaborate with cross-functional teams and communicate technical details clearly.

Preferred Qualifications

• Microsoft Certified: Windows Server Hybrid Administrator Associate or similar.
• Experience in large-scale server migrations and automation projects.
• Familiarity with ITIL processes and change management.

Tags for Posting

Windows2016, Upgrade, Automation, VMware, AWS, Azure, BigFix, Splunk, CyberArk, SCOM, CrowdStrike, Morphisec