Windows Server Architect

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

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 maintain the project Risk Register.
• Produce architecture artifacts (Implementation Blueprint, design documents, runbooks) in Confluence and Jira, ensuring alignment with the client's Technical Reference Model and audit, vulnerability requirements.

Minimum Qualifications

• Bachelor's degree and 7 years of relevant experience.
• An additional 2 years of experience (9 years total) with an Associate's Degree in lieu of a Bachelor's Degree.
• An additional 4 years of experience (11 years total) with a High School Diploma in lieu of a Bachelor's Degree.
• Demonstrated experience leading Windows Server 2016 to 2019 or 2025 migrations in AWS (GovCloud experience preferred), including upgrade planning, testing, and rollback.
• Hands-on Windows Server OS hardening experience using federal and industry baselines.
• Experience integrating Windows servers with CyberArk for privileged access management.
• Deep Windows Server expertise (Active Directory, Group Policy, DNS, DHCP, PKI, patching, Remote Desktop Service) and strong PowerShell skills.
• Working knowledge of AWS services for Windows workloads (EC2, AMIs, VPC, Systems Manager, EBS snapshots).
• Experience with windows configuration management using Ansible (WMI, WinRM, PowerShell)
• Strong technical leadership and communication skills, with the ability to direct engineers and lead discussions with federal stakeholders.

Preferred Qualifications or Skills

• Microsoft Windows Server certification: Microsoft Certified: Windows Server Hybrid Administrator Associate, or the legacy MCSE: Core Infrastructure; equivalent hands-on experience may be considered.
• AWS certification (e.g., AWS Certified Solutions Architect - Associate or Professional).
• Experience with AWS Systems Manager (Automated system patching)
• Experience in managing software deployments through group policy.
• Experience with Microsoft Power BI, including Power BI Gateway administration.
• Experience configuring and hardening Windows IIS servers1.
• Experience supporting federal government systems with audit and vulnerability management.

Position Details

• Employment type: Full-Time, W2
• Location: 100% Remote (US-based)
• Hours: 40 hours/week with availability during core business hours of 8am-5pm ET
• Eligibility: Must be eligible to obtain a Public Trust clearance