Lead Associate Principal, Infrastructure Innovation & Automation

The OCC • Chicago, IL

7d • Hybrid

About The Position

The Lead Associate Principal, Infrastructure Innovation & Automation is a senior technical resource responsible for designing, implementing, and optimizing enterprise infrastructure solutions with a strong emphasis on automation, platform engineering, operational excellence, and infrastructure modernization. This role requires hands-on expertise across Linux and Windows platforms, cloud technologies, CI/CD pipelines, Infrastructure-as-Code (IaC), and automation frameworks. The position bridges strategic technical planning with hands-on execution and is expected to independently lead complex initiatives that improve scalability, reliability, security, and operational efficiency across OCC’s technology landscape.

Requirements

• 10+ years of infrastructure engineering, platform engineering, DevOps, automation engineering, or related experience with increasing technical responsibility
• Strong experience supporting Windows and/or Linux server environments, cloud infrastructure, and enterprise platform technologies.
• Demonstrated ability to independently design, implement, and operationalize scalable infrastructure and automation solutions.
• Proven track record of identifying automation opportunities and driving measurable operational improvements.
• Strong communication and stakeholder management skills with the ability to work effectively across multiple technical disciplines and organizational boundaries.
• Strong experience with Ansible, Terraform Enterprise (TFE), Terraform and Infrastructure-as-Code (IaC) methodologies.
• Hands-on experience developing and supporting CI/CD pipelines using GitHub Actions or similar automation platforms.
• Experience with AWS cloud services, cloud automation, and infrastructure provisioning.
• Strong scripting and automation skills using PowerShell, Python, Bash, or similar languages.
• Experience with Windows and/or Linux server administration, troubleshooting, and automation.
• Knowledge of enterprise endpoint management platforms such as SCCM/MECM, ManageEngine, or equivalent technologies.
• Experience with Kubernetes, OpenShift, and cloud-native technologies.
• Strong understanding of networking, security, storage, virtualization, and enterprise infrastructure architecture.
• Familiarity with Artifactory, source control platforms, and DevOps toolchains.
• Experience working in regulated environments with security, compliance, and governance requirements.
• Bachelor’s degree in computer science, Information Technology, Engineering, or a related field, or equivalent combination of education and relevant work experience.

Nice To Haves

• HashiCorp Terraform Associate
• AWS Solutions Architect Associate or Professional
• Certified Kubernetes Administrator (CKA)
• Red Hat Certified Engineer (RHCE)
• ITIL Foundation Certification
• Microsoft Windows Server or Cloud Infrastructure Certifications

Responsibilities

• Design, implement, and support scalable infrastructure solutions with a focus on automation, resilience, security, and operational efficiency.
• Develop and maintain Infrastructure-as-Code (IaC) solutions using tools such as Ansible and Terraform Enterprise (TFE).
• Design, implement, and support CI/CD pipelines and automation workflows across AWS, and on-premises infrastructure environments.
• Drive automation initiatives for server provisioning, application deployment, configuration management, compliance enforcement, and operational processes.
• Contribute to infrastructure modernization efforts, including Windows and Linux platform automation, cloud adoption, and platform engineering initiatives.
• Design and implement automation solutions utilizing GitHub Actions, Ansible Automation Platform (AAP), Terraform Enterprise, and related DevOps tooling.
• Support enterprise endpoint management and patching initiatives, including SCCM redesign, ManageEngine implementation, and Windows platform automation.
• Collaborate with Infrastructure Engineering, Security, Platform Engineering, Application Development, and Operations teams to identify and implement automation opportunities.
• Lead proof-of-concept (POC) activities, technical evaluations, and pilot implementations for new technologies and solutions.
• Act as a technical lead on assigned initiatives, driving projects from requirements gathering through implementation and operational transition.
• Identify process inefficiencies and proactively recommend automation-driven solutions that improve operational effectiveness.
• Evaluate infrastructure performance, reliability, and scalability, and provide recommendations for continuous improvement.
• Ensure infrastructure solutions comply with OCC security, regulatory, governance, and operational standards.
• Provide technical leadership, mentoring, and guidance to engineers and project teams.
• Serve as a technical escalation point for complex infrastructure, automation, and platform-related issues.

Benefits

• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Senior