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Request Technology, LLC

Windows Server Engineer (Terraform, CICD, Kubernetes)

Hybrid

Chicago, United states

$ 170,000 /year

Full Time

22-12-2025

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Skills

Python Bash PowerShell Firewalls CI/CD Kubernetes Jenkins Ansible VMware Networking Windows Virtualization AWS AWS Cloud CI/CD Pipelines Windows Server 2016 Active Directory TCP/IP Terraform Windows Server

Job Specifications

***Hybrid, 3 days onsite, 2 days remote***

***We are unable to sponsor as this is a permanent full-time role***

A prestigious company is looking for a Windows Administrator (AWS, VMware, CICD, Automation). This role is focused on AWS/On-prem Windows server 2016, 2019, 2022 administration, CICD pipeline automation, Terraform, Ansible, Jenkins, VMware, etc.

Responsibilities:

Administer, support, and optimize Windows Server environments (2016, 2019, 2022) across on-prem and AWS.
Design and maintain automated CI/CD pipelines for server builds and AMIs using Jenkins, Terraform, Ansible, and Packer.
Manage hybrid infrastructure including VMware-based virtualization (vSphere, ESXi, vCenter) and AWS cloud workloads.
Troubleshoot complex system, OS, and application issues; collaborate with vendors and cross-functional teams for resolution.
Automate infrastructure provisioning, patching, and operational tasks to reduce manual effort and increase reliability.
Participate in security patching, hardening, and vulnerability remediation.
Provide input on infrastructure modernization initiatives, including container platforms (Kubernetes as a plus).

Qualifications

Bachelor s degree in computer science, Information Technology, or related field preferred.
Professional Experience: 7+ years of Windows Server engineering and infrastructure support in enterprise environments, with at least 2 3 years in hybrid (on-prem + AWS) environments.
Platform Skills: Strong Windows Server expertise; experience with VMware, AWS, and hybrid infrastructure. Exposure to Kubernetes/container platforms is a plus.
Solution Design: Proven ability to build automated, reliable, and secure infrastructure solutions leveraging IaC and CI/CD pipelines.
Advanced administration of Windows Server 2016, 2019, 2022.
Hands-on experience with CI/CD pipelines and automation (Terraform, Ansible, Jenkins, Packer).
Experience building and maintaining custom AMIs and golden images.
VMware administration (vSphere, ESXi, vCenter) and virtualization concepts.
AWS experience with EC2, networking, and hybrid integrations.
PowerShell scripting; experience with Python or Bash scripting is a plus.
Active Directory and Group Policy administration.
Networking fundamentals (TCP/IP, DNS, DHCP, VLANs, firewalls, load balancers).
Vulnerability remediation and patch management experience.

About the Company

With over 39 years of experience, Request Technology, LLC, formerly Quest Enterprises, Inc., is an established entrepreneurial executive search firm that specializes in recruiting Information Technology professionals for organizations throughout the United States. Extensive industry knowledge and long term working relationships offer the ability to know exactly what our clients need, providing them with the best available candidates in today's competitive job market. Request Technology, LLC consists of a group of Associate R... Know more