The Options Clearing-posted 3 months ago
$133,800 - $187,100/Yr
Full-time • Senior
Hybrid • Chicago, IL
1,001-5,000 employees
Securities, Commodity Contracts, and Other Financial Investments and Related Activities

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.

  • 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 OCC's 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.
  • 7+ years of Windows Server engineering and infrastructure support in enterprise environments, with at least 2-3 years in hybrid (on-prem + AWS) environments.
  • Strong Windows Server expertise; experience with VMware, AWS, and hybrid infrastructure.
  • Proven ability to build automated, reliable, and secure infrastructure solutions leveraging IaC and CI/CD pipelines.
  • Strong teamwork, communication, and ability to partner with application, DevOps, and security teams.
  • Exposure to Kubernetes/container platforms.
  • Experience with PowerShell scripting; experience with Python or Bash scripting is a plus.
  • A hybrid work environment, up to 2 days per week of remote work
  • Tuition Reimbursement to support your continued education
  • Student Loan Repayment Assistance
  • Technology Stipend allowing you to use the device of your choice to connect to our network while working remotely
  • Generous PTO and Parental leave
  • 401k Employer Match
  • Competitive health benefits including medical, dental and vision
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