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Addison Group

Lead Infrastructure Innovation & Automation Engineer

Addison Group, Chicago, Illinois, United States, 60290

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Lead Infrastructure Innovation & Automation Engineer Location:

Chicago, IL — Hybrid (3 days onsite per week)

Salary Target:

Up to $165,000 base

Benefits:

Full-time role, eligible for benefits

Overview We are seeking a highly skilled

Infrastructure & Automation Engineer

to lead the design, implementation, and support of hybrid infrastructure solutions across both on‑premise and AWS environments. This role is ideal for an engineer with deep, hands‑on experience in Windows Server, VMware, automation frameworks, infrastructure‑as‑code, and CI/CD methodologies.

The position emphasizes innovation, automation, and operational excellence—requiring strong technical leadership and the ability to collaborate across engineering, DevOps, and security teams.

What You’ll Do

Administer, support, and optimize

Windows Server environments (2016/2019/2022)

across on‑prem and AWS.

Design, build, and maintain

automated CI/CD pipelines

for server builds and AMIs using

Jenkins, Terraform, Ansible, and Packer .

Manage and support hybrid infrastructure including

VMware virtualization technologies

(vSphere, ESXi, vCenter) and AWS workloads.

Troubleshoot complex OS, system, and application issues; partner with cross‑functional teams and vendors for resolution.

Automate infrastructure provisioning, patching, image creation, and operational activities to increase efficiency and reliability.

Participate in system hardening, security patching, and vulnerability remediation efforts.

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

Contribute to modernization initiatives including container platforms; exposure to

Kubernetes

is highly valuable.

Participate in after‑hours maintenance or support as needed.

Supervisory Responsibilities

No direct reports, but expected to mentor peers, provide technical guidance, conduct knowledge sharing, and influence engineering standards.

Qualifications Professional Experience

7+ years

of Windows Server engineering and enterprise infrastructure support.

2–3+ years

supporting hybrid environments (on‑prem + AWS).

Must have originated from a

true infrastructure background —not purely DevOps‑focused roles.

Platform & Solution Expertise

Strong experience with:

Windows Server administration

VMware virtualization technologies

AWS (EC2, networking, hybrid integrations)

Proven ability to build automated, reliable, and secure infrastructure solutions using IaC and CI/CD pipelines.

Experience with Kubernetes or container ecosystems considered a plus.

Technical Skills

Windows Server 2016/2019/2022 administration (advanced level).

Infrastructure‑as‑Code & automation tools:

Terraform

Ansible

Jenkins

Packer / AMI image management

VMware (vSphere, ESXi, vCenter)

AWS compute, networking, and hybrid cloud services

PowerShell scripting; Python or Bash scripting preferred

Active Directory / Group Policy

Networking fundamentals (TCP/IP, DNS, DHCP, VLANs, firewalls, load balancers)

Vulnerability remediation and patch management experience

Kubernetes or container experience (preferred)

Education

Bachelor’s degree in Computer Science, IT, or a related field preferred

Equivalent experience accepted

Certifications (Preferred)

Microsoft: Windows Server or Azure certifications

VMware: VCP-DCV or comparable

AWS: Solutions Architect – Associate or similar

Terraform, Ansible, or other automation‑focused certifications

Additional Profile Notes

Ideal candidates have

8–10 years of hands‑on infrastructure engineering experience .

Must be strong across

at least two or three key domains

such as Terraform, Ansible, Jenkins, Kubernetes, and AWS.

Expected to lead automation and innovation initiatives across Windows, VMware, storage, and broader infrastructure areas.

Must be able to design solutions, build automation, and then hand off stable, documented work to ongoing operations teams.

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