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 architectural decisions that balance reliability, performance, and cost efficiency across the platform.
• Incremental Delivery: Help the team break down complex work into vertical slices, ensuring incremental value delivery and fast feedback loops.
• Mentorship Team Growth: Mentor engineers across engineering in networking fundamentals, DevOps best practices, and system design at scale. Contribute to hiring, onboarding, and upskilling initiatives within the DevOps organization.

By the end of your first year:

Establish yourself as a strategic leader and mentor, driving long-term infrastructure transformation and intelligent automation across the engineering organization.

• Strategic Leadership Modernization: Lead large-scale modernization initiatives to simplify and scale cloud networking and edge architecture. Help define and execute the long-term vision for infrastructure transformation integrating AI-driven intelligence into monitoring, alerting, and delivery pipelines. Partner with engineering leadership to align infrastructure strategy with organizational goals and developer productivity.
• Promote Team Ownership: Foster a culture where each team member feels empowered to take initiative and contribute to the team’s success. Create sustainable patterns and tooling that accelerate delivery without increasing risk.
• Mentor Develop Peers: Continue mentoring engineers at all levels, fostering a culture of technical excellence, intelligent automation, and continuous improvement. Help shape team structures, processes, and priorities to sustain long-term transformation.
• Help Shape Team Strategy: Share thought leadership on automation, modernization, and AI enablement within OpenSesame and the wider engineering community.
• Continuous Improvement Innovation: Evaluate emerging tools and services in networking, edge delivery, and cloud security to drive further optimization. Lead or partner in proofs of concept in areas such as AI-assisted deployment, multi-region failover, edge compute, and zero-trust networking.

Technology Stack

Our tech stack is outlined below; however, we strongly believe in using the right technology for a given job and in constantly experimenting to see what new technology can do for us. That being said we have systems using or implemented in:

• Terraform
• AWS including AWS Networking and AWS WAF
• Fastly
• Github Actions
• Docker
• Chef
• Python
• Docker
• PHP
• Go
• C#

Location: This position can be based anywhere in the US. We operate as a remote-first company, and invest in mandatory all-company meetings several times a year in addition to required team travel as necessary.

Performance Driven: We're looking for self-starters with a track record of delivering excellent results, but we're highly selective about who we hire. We don't focus on typical job requirements, instead, we're interested in specific examples from your past experiences. All positions can be based anywhere in the US, and require up to 15 days of travel per year, with senior management and leadership teams requiring up to 35 days.

Compensation: The base salary for this position generally ranges between $170,000 and $208,000, depending on experience. At OpenSesame, we offer a comprehensive benefits package to employees upon hire, including professional development, ISOs, health insurance, 401(k) matching, and paid time off.

Equal Employment Opportunity: OpenSesame is an Equal Employment Opportunity and Affirmative Action employer that values and welcomes diversity. We do not discriminate on the basis of various legally protected characteristics, including criminal history, and strive to provide reasonable accommodations to qualified individuals with disabilities. We prioritize safety and security and may use your information accordingly, and you can contact us for assistance or accommodations during the job application process.

Pay Transparency: At OpenSesame, we prioritize pay transparency, fairness, and equity to create a positive and inclusive work environment, regularly reviewing our compensation practices to align with our values and goals. We provide competitive and fair compensation to our employees based on their skills, experience, and performance.

We Care About Your Security: We’ve been made aware of a phishing scam involving individuals impersonating OpenSesame recruiters. All legitimate communication from our team will come from @opensesame.com email addresses. If you receive a suspicious message, please contact us directly at careers@opensesame.com. Your security matters to us — thank you for staying vigilant.