Remote AWS Windows Infrastructure Automation Engineer

Phoenixoutcomes; Northern (KY); Remote; USD 110,000 - 150,000; Full time

Job summary

Phoenixoutcomes is seeking an AWS Windows Infrastructure Engineer to automate configuration, deployment, and hardening of Windows Server environments hosted in a FedRAMP-authorized AWS GovCloud. The role supports upgrades from Windows Server 2016 to 2019 or 2025 and reports to the Windows Architect.

Responsibilities include building hardened AMIs, automating patching and compliance, and integrating automation into CI/CD tools such as Jenkins and GitHub.

Qualifications

• Bachelor's degree and 5 years of relevant experience.
• An additional 2 years of experience (7 years total) with an Associate's Degree in lieu of a Bachelor's Degree.
• An additional 4 years of experience (9 years total) with a High School Diploma in lieu of a Bachelor's Degree.
• Hands-on experience automating Windows Server configuration with Ansible, PowerShell DSC, or similar tools.
• Advanced PowerShell scripting skills.
• Experience supporting Windows Server 2016 to 2019 or 2025 upgrades or migrations in AWS.
• Experience automating Windows OS hardening, preferably in regulated federal or regulated industry.
• Working knowledge of AWS services for Windows workloads (EC2, AMIs, VPC, Systems Manager, EBS snapshots).
• Solid Windows Server administration skills (Active Directory, Group Policy, DNS, certificates, patching).
• Experience with infrastructure-as-code tools (e.g., Terraform, CloudFormation) or image-building tools (e.g., Packer, EC2 Image Builder).
• Experience with Git-based version control and CI/CD pipelines in an Agile, DevSecOps environment.

Responsibilities

• Automate Windows Server configuration, build, and deployment using Ansible and PowerShell scripting.
• Update Windows Server 2016 baselines to 2019/2025 standards and correct drift.
• Build and maintain hardened Windows AMIs and automate EC2 provisioning.
• Automate OS hardening and compliance checks (DISA STIGs, CIS Benchmarks) and remediate findings.
• Execute upgrades in phased waves with pre/post checks and automated rollback.
• Automate patching, inventory, and tasks using AWS Systems Manager.
• Automate certificate installation and renewal for upgraded servers.
• Integrate Windows automation into CI/CD pipelines with version-controlled code.
• Document automation, configurations, and runbooks in Confluence and track in Jira.

Skills

PowerShell

Ansible

Windows Server

AWS

Scripting

Git

CI/CD

Jenkins

GitHub

Education

Bachelor's degree

Associate's Degree in lieu of Bachelor's

High School Diploma in lieu of Bachelor's

Tools

PowerShell DSC

Terraform

CloudFormation

Packer

EC2 Image Builder

Job description

Phoenixoutcomes is seeking an AWS Windows Infrastructure Engineer to automate configuration, deployment, and hardening of Windows Server environments hosted in a FedRAMP-authorized AWS GovCloud. The role supports upgrades from Windows Server 2016 to 2019 or 2025 and reports to the Windows Architect.

Responsibilities include building hardened AMIs, automating patching and compliance, and integrating automation into CI/CD tools such as Jenkins and GitHub.