Staff DevOps Software Engineer

About OpenSesame

OpenSesame is transforming workforce development with an AI-powered marketplace of 60,000+ skill-building courses and learning pathways. We help organizations build skills and stay compliant through a high-quality content catalog, seamless LMS/LXP integrations, and advanced capabilities like skills-based curation and multilingual content creation. More than 2,000 companies, including 150+ of the Global 2000, rely on OpenSesame to develop the world’s most productive and admired workforces.

Learn more: www.opensesame.com/about

About the Team 

The DevOps team at OpenSesame designs, builds and operates the automation, cloud infrastructure, and edge systems that power our global learning platform. We’re a collaborative, forward-thinking group focused on scalability, security, and reliability. Now, we’re expanding our focus toward intelligent automation and developer enablement, creating smarter systems and workflows that help every engineer at OpenSesame deliver faster and more confidently.

About the Job

We’re seeking an experienced Staff DevOps Engineer with expertise in enterprise-scale AWS networking, edge infrastructure, and platform transformation to join our remote U.S.-based team. You’ll lead strategic initiatives to modernize and automate OpenSesame’s infrastructure, driving greater intelligence, resilience, and scalability across our global learning platform.

You’ll partner across teams to embed automation, reliability, and intelligent systems into everything we do, helping shape how AI and and intelligent automation are explored and applied throughout the software delivery lifecycle (SDLC) from CI/CD and observability to operational insights and developer enablement.

Success requires both hands-on AWS and automation expertise and the strategic vision and mindset to simplify systems, guide direction, and empower developers.  If you’re passionate about large-scale infrastructure, edge performance, and the potential of intelligent tooling and you want to help define what modern DevOps looks like at scale,  we’d love to hear from you.

Performance Objectives:

In your first 90 days:

Build context, relationships, and credibility as a strategic and technical leader. Deeply understand OpenSesame’s AWS networking, edge delivery, and automation landscape. Identify transformation opportunities where intelligent automation and AI-assisted tooling can enhance reliability, scalability, and developer productivity.

• Team Integration & Shared Ownership: Build strong relationships across our engineering teams. Develop a deep understanding of our AWS account structure, VPC architecture, routing patterns, edge systems, and WAF configurations. Engage in team ceremonies and adopt shared ownership of infrastructure reliability.
• Technical Contribution: Deliver early improvements in network and edge configurations, focusing on automating provisioning with Terraform. Identify opportunities for AI-enabled observability or workflow automation that reduce manual effort and improve response time. Begin defining an architectural vision for future-state network and edge automation.
• Mentorship & Skill Development: Share expertise on AWS networking and edge design patterns within engineering through documentation and collaborative sessions. Mentor engineers on DevOps and infrastructure security best practices. Explore and share learnings on AI-assisted development and automation tools.
• Improve Team Processes: Engage fully in the team's agile ceremonies, retrospectives, and discussions to streamline operations. Identify and help remove friction in managing network and edge configurations. 

Within 6 months:

Lead high-impact initiatives that improve performance, reliability, and developer enablement while influencing long-term platform direction.

• Ownership: Lead modernization efforts in AWS networking, edge security, and delivery systems, emphasizing automation, observability, and scalability. Pilot AI-assisted tooling to enhance CI/CD pipelines, anomaly detection, and configuration drift management.
• Developer Enablement: Build self-service workflows that allow developers to safely deploy or modify network and edge configurations. Integrate automation and intelligent tooling into CI/CD workflows, monitoring, and remediation pipelines.
• Strategic Leadership: Collaborate with engineering leadership to shape the technical roadmap for infrastructure modernization and intelligent developer enablement. Influence