Lead DevOps Engineer (DevSecOps Transformation)

Lead DevOps Engineer (DevSecOps Transformation) – Chicago, IL

Location: Chicago, IL (100% Onsite)

Salary: Up to $200,000 Base Salary

Employment Type: Full-Time, Permanent

Sponsorship Available

Relocation Candidates Welcome

Are you a DevOps leader who thinks beyond pipelines and automation? Do you have experience driving DevSecOps strategy, cloud transformation, and AI adoption across enterprise engineering organizations?

We're seeking a Lead DevOps Engineer to help shape the future of software delivery for a highly regulated financial institution. This role is ideal for someone who can establish vision, influence engineering teams, drive modernization initiatives, and champion DevSecOps best practices at scale.

This is not simply a build-and-support role. We're looking for a strategic leader who can help define what modern DevOps should look like across the organization.

What You'll Do

• Lead enterprise-wide DevSecOps initiatives and adoption strategies.
• Define standards, governance, and best practices for CI/CD and software delivery.
• Drive migration efforts involving source control, application lifecycle management, and deployment tooling.
• Partner with Development, Infrastructure, Security, Architecture, and Cloud teams to modernize delivery processes.
• Design scalable CI/CD frameworks leveraging Azure DevOps, GitHub, GitHub Actions, and cloud-native technologies.
• Champion AI-enabled software development practices using GitHub Copilot and related technologies.
• Evaluate how AI can accelerate development, testing, documentation, and operational efficiency while maintaining security and regulatory compliance.
• Build metrics and dashboards to measure DevSecOps maturity and adoption.
• Mentor engineers and influence Agile product teams across the organization.
• Evangelize DevSecOps culture through Centers of Excellence (CoE) and cross-functional initiatives.

Required Experience

• 7+ years of senior-level DevOps, Platform Engineering, or Software Engineering experience.
• Deep expertise with CI/CD platforms including Azure DevOps, GitHub Actions, Jenkins, TeamCity, Bamboo, or Octopus.
• Strong cloud engineering experience with AWS.
• Expertise with Terraform, Ansible, Docker, Podman, Helm, and Kubernetes/EKS.
• Experience integrating security into the SDLC using tools such as Checkmarx, SonarQube, Prisma Cloud, or similar platforms.
• Strong scripting and automation skills with Python, PowerShell, and Bash.
• Experience implementing Infrastructure as Code and automated testing strategies.
• Experience administering and optimizing GitHub Copilot.
• Knowledge of Agile, Scrum, and modern software delivery methodologies.
• Strong communication and leadership skills with the ability to influence teams and executive stakeholders.

Preferred Experience

• Financial services, banking, or other highly regulated environments.
• Enterprise-scale DevSecOps transformations.
• AI governance and secure AI implementation within software development lifecycles.
• Experience creating engineering standards, governance models, and operating frameworks.

Why This Role?

You'll help define the future state of DevSecOps for a major financial institution, driving initiatives around automation, developer productivity, security integration, cloud modernization, and AI adoption. This is a highly visible leadership role with significant influence across engineering teams.

Please note: This role requires onsite attendance in Chicago. Candidates outside the area who are willing to relocate are encouraged to apply. Sponsorship is available for qualified candidates.