Lead Windows AWS Automation Engineer (Chicago)

Prestigious Financial Institution is currently seeking a Lead Windows and AWS Automation Engineer. Candidate will be 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.

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.

Ensure infrastructure aligns with compliance, audit, and change management standards.

Provide input on infrastructure modernization initiatives, including container platforms (Kubernetes as a plus).

Support on after-hours maintenance as needed.

Qualifications

Professional Experience : 7+ years of Windows Server engineering and infrastructure support in enterprise environments, with at least 23 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.

Certificates or Licenses

Relevant certifications preferred :

Microsoft (Windows Server, Azure Administrator)

VMware (VCP-DCV or similar)

AWS (Solutions Architect Associate or equivalent)

Terraform / Ansible or other automation-related certifications