Staff DevOps Engineer (AWS Networking, Terraform, Cloud Infrastructure) - Remote US

About OpenSesame: AI-Powered Workforce Development

OpenSesame is transforming workforce development using an AI-powered marketplace featuring over 60,000 skill-building courses and learning pathways. We help organizations build skills and maintain compliance 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 over 150 of the Global 2000, rely on OpenSesame to develop productive workforces.

Learn more: www.opensesame.com/about

The DevOps Team

The DevOps team designs, builds, and operates the automation, cloud infrastructure, and edge systems powering our global learning platform. We are focused on scalability, security, and reliability. We are expanding our focus toward intelligent automation and developer enablement, creating smarter systems and workflows to help every engineer deliver faster and more confidently.

Staff DevOps Engineer (AWS Networking & Platform Transformation)

We are seeking an experienced Staff DevOps Engineer specializing in enterprise-scale AWS networking, edge infrastructure, and platform transformation to join our remote U.S.-based team. This role involves leading strategic initiatives to modernize and automate OpenSesame's infrastructure, driving greater intelligence, resilience, and scalability across the global learning platform.

You will partner across teams to embed automation, reliability, and intelligent systems, helping shape how AI and intelligent automation are applied throughout the Software Delivery Lifecycle (SDLC), from CI/CD and observability to operational insights and developer enablement. Success requires hands-on AWS and automation expertise combined with the strategic vision to simplify systems, guide direction, and empower developers.

Performance Objectives:

In your first 90 days:

• Context Building: 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 engineering teams. Develop a deep understanding of our AWS account structure, VPC architecture, routing patterns, edge systems, and WAF configurations. 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. Begin defining an architectural vision for future-state network and edge automation.
• Mentorship & Skill Development: Share expertise on AWS networking and edge design patterns 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.
• Process Improvement: Engage fully in agile ceremonies, retrospectives, and discussions to streamline operations. Help remove friction in managing network and edge configurations.

Within 6 months:

• 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 allowing 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.
• 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.

By the end of your first year:

• 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.
• Promote Team Ownership: Foster a culture where each team member feels empowered to take initiative and contribute. Create sustainable patterns and tooling that accelerate delivery without increasing risk.
• Mentor & Develop Peers: Continue mentoring engineers at all levels, fostering technical excellence, intelligent automation, and continuous improvement. Help shape team structures, processes, and priorities.
• 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. 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:

We believe in using the right technology for the job and constantly experimenting. Systems are currently using or implemented in:

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

Location, Compensation, and Benefits:

This position is remote-first and can be based anywhere in the US. Travel of up to 15 days per year is required (senior management/leadership teams require up to 35 days).

The base salary generally ranges between $170,000 and $208,000, depending on experience. We offer a comprehensive benefits package including professional development, ISOs, health insurance, 401(k) matching, and paid time off.

OpenSesame is an Equal Employment Opportunity and Affirmative Action employer. We prioritize safety and security. All legitimate communication will come from @opensesame.com email addresses.