Lead DevOps Engineer

At the Federal Home Loan Bank of Chicago, employees come first – that’s why we offer a highly competitive compensation and bonus package, along with access to a comprehensive benefits program designed to meet the needs of our employees.

• Collaborative, in‑office operating model
• Retirement program (401k and Pension)
• Medical, dental and vision insurance
• Lifestyle Spending Account
• Competitive PTO plan
• 11 paid holidays per year

Who we are

Our mission at FHLBank Chicago: to partner with our members in Illinois and Wisconsin to provide competitively priced funding, a reasonable return on their investment, and support for their community investment activities. Simply said, we’re a bank for banks and other financial institutions, focused on being a strategic partner for our members and working together to reinvest in our communities, from urban centers to rural areas. Created by Congress in 1932, FHLBank Chicago is one of 11 Federal Home Loan Banks, government‑sponsored in support of mortgage lending and community investment.

What it's like to work here

At FHLBank Chicago, we bring people together. We are committed to a high‑performing, engaged workforce and to supporting the communities we serve across Illinois and Wisconsin. Our Buddy Program pairs new hires with tenured employees to guide their onboarding. Our professional development and training opportunities—including upskilling, mentorship programs and tuition reimbursement—allow employees to grow their career with us. Our collaborative, in‑office operating model fosters innovation, connection and shared success. To support balance and flexibility, employees receive an allocation of remote days to use as needed throughout the year.

What You'll do

The Lead DevOps Engineer serves as a leader and hands‑on technical expert, driving the implementation and scaling of DevSecOps practices across the Bank’s technology landscape. The role partners closely with IT Delivery Teams to ensure that code, services and products transition seamlessly from development through deployment and into production.

In addition to deep technical expertise in automation, scripting and continuous integration, the Lead DevOps Engineer builds out the necessary processes, frameworks and tools to support enterprise‑wide DevSecOps adoption. Responsibilities include designing scalable CI/CD pipelines, embedding security into every phase of the software development lifecycle and fostering a culture of collaboration and continuous improvement.

The successful candidate will demonstrate strong leadership in guiding cross‑functional teams—including development, infrastructure, security and architecture—toward modern engineering practices. They will proactively identify opportunities for innovation, standardization and automation, mentor teams and champion the adoption of DevSecOps principles.

How you'll make an impact:

• Enhancing Automation and Efficiency: Implement and manage CI/CD pipelines, automate infrastructure provisioning and ensure seamless integration and deployment, thereby enhancing overall efficiency and reducing time‑to‑market for new features and services.
• Strengthening Security and Compliance: Implement security best practices and ensure compliance with performance, security, availability and recoverability standards, safeguarding the bank’s IT infrastructure and maintaining operational integrity.
• Fostering Innovation and Collaboration: Drive the adoption of DevSecOps culture across Agile product delivery teams, mentor junior engineers and collaborate with various teams to design and deploy innovative solutions, contributing to the bank’s technological advancement and competitive edge.

What you can expect:

• Setup CI/CD pipelines supporting automated deployment of resources to Cloud environments at medium to high complexity.
• Strategic focus on scaling DevOps practices within an enterprise.
• Supervise design, implementation and management of CI/CD pipelines.
• Automate infrastructure provisioning and configuration.
• Collaborate with development teams to ensure seamless integration and deployment.
• Implement security best practices and ensure compliance.
• Proactively identify system and process risks and recommend or implement improvements.
• Develop, implement and support test automation for continuous integration and delivery.
• Identify and develop metrics and dashboards to monitor adoption and maturity of DevSecOps practice.
• Expertise in containerization (Docker and Podman) and orchestration via AWS Elastic Kubernetes Service (EKS).
• Manage and mature the Bank’s software development life‑cycle (SDLC) ensuring alignment with Agile, DevSecOps and platform standards.
• Embed shift‑left security practices leveraging tools such as Checkmarx, SonarQube and PrismaCloud.
• Identify and implement opportunities for automation, standardization and process enhancements.
• Provide technical guidance and mentoring to software delivery teams and junior engineers to promote cross‑functional knowledge sharing.
• Contribute to architecture discussions around technology controls in a DevSecOps/Cloud environment.
• Collaborate with architecture, security and delivery teams to estimate, design, code, deploy and support working software components.
• Foster the adoption of DevSecOps culture and capabilities across Agile product delivery teams.
• Liaison with Delivery teams to support necessary configurations/set‑up in Azure DevOps (ADO) for Agile.
• Participate in technology Center of Excellence and evangelize DevSecOps methodologies.
• Work with development and support teams to design improved deployment, provisioning and integration workflows, ensuring environment stability and identifying improvement plans.
• Contribute to technology, vendor package and tool road‑mapping, evaluation and introduction.
• Ensure compliance with performance, security, availability, recoverability standards and provide monitoring recommendations.

What you'll bring:

• 7+ years of demonstrable software engineering and DevOps experience.
• 7+ years working in SCRUM/Agile software development environment.
• Experience deploying and administering CI tools such as Azure DevOps, Jenkins, TeamCity, Octopus or Bamboo.
• Expertise with infrastructure cloud tools such as Terraform, Docker, Podman, Helm etc.
• Experience administering and integrating SAST tools (Checkmarx) and code quality tools (SonarQube).
• Expertise with integrating automated testing solutions for unit, system, integration and performance testing within CI/CD.
• Bachelor’s Degree or equivalent experience. Computer Science or related field preferred.
• Strong cloud engineering experience primarily with Amazon Web Services (AWS).
• Expertise with Terraform, Ansible and/or Chocolaty for infrastructure automation and configuration.
• Expertise with containerization via Docker and Podman and orchestration with Amazon EKS.
• Expertise with GitHub Copilot configuration and administration.
• Expertise with programming languages such as Python, PowerShell and Bash (must).
• Expertise with Application Performance Monitoring (APM) tools such as Datadog and SolarWinds.
• Expertise with project management and workflow tools and concepts such as Agile, Scrum/Kanban, etc.
• Proficiency in cross‑platform scripting languages and build tools (Python, Artifactory, MS Build, NuGet).
• Proficiency in OOP software development using C# or similar languages.
• Ability to define scalable and secure CI/CD pipelines.
• Deep understanding of containerization strategies using Docker and Podman.
• Experience with pair programming using GitHub Copilot.
• Strong communication/presentation skills and ability to build and explain standards, processes and cloud architecture with team and management.

The Perks

At FHLBank Chicago, we offer a highly competitive compensation and bonus package, and a comprehensive benefits program designed to meet the needs of our employees. Retirement benefits include a 401(k) and pension plan. Our wellbeing program supports employees at work and in their personal lives: five weeks of vacation, 11 paid holidays per year, and a Lifestyle Spending Account providing an annual stipend for wellbeing activities. Location at the Old Post Office offers easy access to public transportation and rooftop views. For more details, visit the benefits portal.

Salary Range

$108,450.00 - $180,825.00

The above represents the expected salary range for this job requisition. Ultimately, in determining your pay, we may also consider your experience and other job‑related factors. In addition to the base salary, we offer a comprehensive benefits package which can be found here: