Windows Server Architect

Windows Server Architect Overview The Windows Server Architect leads the design and technical direction for migrating a federal client's Windows Server estate, hosted in a FedRAMP-authorized AWS GovCloud environment, from Windows Server 2016 to Windows Server 2019 or 2025 ahead of end of support. As the Windows subject matter expert, the role owns the upgrade architecture end to end, from discovery through hardening, testing, and rollback, and guides DevSecOps, Security, and Test team members to deliver compliant, low-risk upgrades for mission-critical systems. Key Functions Lead discovery of in-scope servers, cataloging roles, services, installed software, and dependencies. Design the upgrade approach for each server (in-place vs. rebuild), including AMI selection, EC2 sizing, and a phased, wave-based sequence with go/no-go checkpoints between waves. Define and validate OS hardening baselines (e.g., DISA STIGs, CIS Benchmarks, Active Directory Domain) and remediate outstanding security findings. Design secure administrative access, including RDP/jump server configuration and CyberArk privileged access integration. Plan certificate management and renewal, including certificate chain validation. Design Windows IIS-dependent workloads, such as Power BI Gateway servers. Partner with DevSecOps Engineers to automate Windows build standards and correct configuration drift. Partner with the Test Manager on each wave's test strategy, success criteria, and rollback procedures, and mai