NO OPT
Lead Associate Principal, Infrastructure Innovation & Automation
You will need at least 8-10 years of experience in working through Terraform, CI/CD, Kubernetes and holding specialization in Windows and Automation tools.
SALARY: $160k - $170k plus 15% bonus
LOCATION: CHICAGO, IL
Hybrid 3 days in office and 2 days onsite
Looking for a candidate with on premises and AWS, Windows server 2016, 2019, 2022, hands on experience CICD pipelines, automation, terraform, ansible, Jenkins. VMware administration vSphere ESXI vcenter AWS EC2 networking hybrid integration
The Lead Associate Principal is responsible for designing, implementing, and supporting hybrid infrastructure solutions across both on-premises and AWS environments, with a strong emphasis on automation, CI/CD, and operational excellence. This role requires hands-on expertise in Windows Server administration, infrastructure-as-code (Terraform, Ansible), image management (Packer/AMI), and virtualization (VMware). Experience with Kubernetes and containerized workloads is a plus. The ideal candidate will blend deep technical skills with a strong focus on automation and collaboration to ensure resilient, scalable, and secure infrastructure.
Primary Duties and 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.
Qualifications
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.
Collaboration: Strong teamwork, communication, and ability to partner with application, DevOps, and security teams.
Technical Skills
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.
Kubernetes/container platform experience a plus.
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