Remote Windows Server Upgrade Architect – FedRAMP AWS

Phoenixoutcomes; Northern (KY); Remote; USD 150,000 - 190,000; Full time

Job summary

Phoenixoutcomes is hiring a Windows Server Architect to lead the end-to-end upgrade of a federal Windows Server estate from 2016 to 2019 or 2025 in a FedRAMP AWS GovCloud environment. You will define upgrade paths, hardening baselines, and secure access controls, coordinating with DevSecOps, Security, and Test teams to ensure compliant, low-risk migrations.

The role requires strong PowerShell skills, AD/GP/DNS expertise, and experience with AWS Windows workloads.

Qualifications

• Bachelor's degree or 7 years of relevant experience.
• Additional 2 years with an Associate's Degree in lieu of a Bachelor's.
• Additional 4 years with a High School Diploma in lieu of a Bachelor's.
• Experience leading Windows Server 2016 to 2019/2025 migrations in AWS GovCloud.
• Hands-on Windows Server OS hardening with federal baselines.
• Experience integrating Windows servers with CyberArk for privileged access management.
• Strong PowerShell and AD/GP/DNS expertise.
• AWS services knowledge for Windows workloads.

Responsibilities

• Lead discovery of in-scope servers, cataloging roles, services, and dependencies.
• Design upgrade approach per server with phased waves and go/no-go checkpoints.
• Define and validate OS hardening baselines and remediate findings.
• Design secure admin access including RDP/jump server and CyberArk integration.
• Plan certificate management and renewal and certificate chain validation.
• Design Windows IIS workloads and Power BI Gateway servers.
• Collaborate with DevSecOps to automate Windows build standards and prevent drift.
• Coordinate test strategy and rollback procedures with the Test team and maintain risk register.
• Produce architecture artifacts like Implementation Blueprint and runbooks.

Skills

Windows server expertise

Leadership

Communication

PowerShell

AWS knowledge

Education

Bachelor's degree

Associate's Degree alternative

High School Diploma alternative

Tools

CyberArk

Ansible

PowerShell

AWS (EC2, AMIs, VPC, SSM)

Job description

Phoenixoutcomes is hiring a Windows Server Architect to lead the end-to-end upgrade of a federal Windows Server estate from 2016 to 2019 or 2025 in a FedRAMP AWS GovCloud environment. You will define upgrade paths, hardening baselines, and secure access controls, coordinating with DevSecOps, Security, and Test teams to ensure compliant, low-risk migrations.

The role requires strong PowerShell skills, AD/GP/DNS expertise, and experience with AWS Windows workloads.