Windows Server Upgrade Engineer

<div><p>Department: Core-IT / Technology</p><p>Contract Type: Project-based (1 yr)</p><h3>Role Overview</h3><p>We are seeking an experienced Windows Server Upgrade Engineer to lead and execute an enterprise-wide upgrade of Windows Server 2016 to Windows Server 2022 or 2025.</p><p>The ideal candidate will have strong hands‑on expertise in server administration, automated provisioning, patching, GPO management, and troubleshooting complex infrastructure issues.</p><h3>Key Responsibilities</h3><ul><li>Plan, execute, and document the end‑to‑end Windows Server upgrade process (2016 → 2022/2025).</li><li>Perform pre‑migration assessments, compatibility checks, and remediation activities.</li><li>Provision new servers using automated deployment technologies</li><li>Implement and oversee patching cycles via SCCM, Azure Update Manager, or similar platforms.</li><li>Coordinate with application SMEs to plan and communicate application downtime, ensuring minimal business impact during upgrade windows.</li><li>Troubleshoot OS‑level and SQL/Windows Cluster issues, AD domain interactions, GPO conflicts, network dependencies, and application compatibility problems.</li><li>Collaborate with security and application teams to ensure compliance and smooth cutover.</li><li>Maintain accurate documentation, upgrade runbooks, rollback steps, and test validations.</li><li>Ensure minimal downtime and strict adherence to change‑management processes.</li></ul><h3>Required Skills&Experience</h3><ul><li>5+ years hands‑on experience in Windows Server administration (2012/2016/2019/2022).</li><li>Proven experience upgrading or migrating Windows Server environments.</li><li>Strong understanding of Active Directory, DNS, DHCP, Failover Clustering, and GPOs.</li><li>Experience with automated server provisioning (PowerShell DSC, SCCM, Azure Automation, Terraform/Ansible optional).</li><li>Deep knowledge of patching tools (SCCM, Azure Update Manager) and experience managing VMware vCenter environments.</li><li>Strong PowerShell scripting skills for automation and troubleshooting.</li><li>Familiarity with virtualization platforms (VMware) with strong ESXi‑specific administration and troubleshooting experience.</li><li>Ability to diagnose performance issues using OS‑level and network‑level tools.</li><li>Experience in enterprise change‑control and documentation practices.</li></ul><h3>Preferred Qualifications</h3><ul><li>Experience with parallel or in‑place upgrade strategies.</li><li>Exposure to cloud‑integrated Windows Server workloads (Azure AD Connect, hybrid joins).</li></ul><h3>Soft Skills</h3><ul><li>Excellent coordination and communication skills, especially when working with application SMEs and business stakeholders.</li><li>Ability to work under pressure during maintenance windows.</li><li>Strong problem solving capability and ownership mindset.</li></ul></div>#J-18808-Ljbffr