Windows Server Upgrade Architect

<p>Department: Core-IT / Technology</p><p>Contract Type: Project-based (1 yr)</p><p>Role Overview</p><p>We are seeking an experienced Windows Server Upgrade Engineer to lead and</p><p>execute an enterprise-wide upgrade of Windows Server 2016 to Windows Server 2022 or</p><p>2025.</p><p>The ideal candidate will have strong hands-on expertise in server administration,</p><p>automated provisioning, patching, GPO management, and troubleshooting complex</p><p>infrastructure issues.</p><p>Key Responsibilities</p><p>• Plan, execute, and document the end-to-end Windows Server upgrade process (2016 → 2022/2025).</p><p>• Perform pre-migration assessments, compatibility checks, and remediation activities.</p><p>• Provision new servers using automated deployment technologies</p><p>• Implement and oversee patching cycles via SCCM, Azure Update Manager, or similar platforms.</p><p>• Coordinate with application SMEs to plan and communicate application downtime, ensuring minimal business impact during upgrade windows.</p><p>• Troubleshoot OS-level and SQL/Windows Cluster issues, AD domain interactions, GPO conflicts, network dependencies, and application compatibility problems.</p><p>• Collaborate with security and application teams to ensure compliance and smooth cutover.</p><p>• Maintain accurate documentation, upgrade runbooks, rollback steps, and test validations.</p><p>• Ensure minimal downtime and strict adherence to change-management processes.</p><p>Required Skills&Experience</p><p>• 5+ years hands-on experience in Windows Server administration (2012/2016/2019/2022).</p><p>• Proven experience upgrading or migrating Windows Server environments.</p><p>• Strong understanding of Active Directory, DNS, DHCP, Failover Clustering, and GPOs.</p><p>• Experience with automated server provisioning (PowerShell DSC, SCCM, Azure Automation, Terraform/Ansible optional).</p><p>• Deep knowledge of patching tools (SCCM, Azure Update Manager) and experience managing VMware vCenter environments.</p><p>• Strong PowerShell scripting skills for automation and troubleshooting.</p><p>• Familiarity with virtualization platforms (VMware) with strong ESXi-specific administration and troubleshooting experience.</p><p>• Ability to diagnose performance issues using OS-level and network-level tools.</p><p>• Experience in enterprise change-control and documentation practices.</p><p>Preferred Qualifications</p><p>• Experience with parallel or in-place upgrade strategies.</p><p>• Exposure to cloud-integrated Windows Server workloads (Azure AD Connect, hybrid joins).</p><p>Soft Skills</p><p>• Excellent coordination and communication skills, especially when working with application SMEs and business stakeholders.</p><p>• Ability to work under pressure during maintenance windows.</p><p>• Strong problem-solving capability and ownership mindset.</p>#J-18808-Ljbffr