Senior DevOps Software Engineer - Remote (Canada)

About OpenSesame

OpenSesame is the trusted partner for workforce reinvention in the age of AI. We deliver integrated software, curated and customizable content, and expert services embedded into existing learning, HR, and work systems to help organizations expand their human + AI potential and thrive through change.

About the Role

We are seeking a DevOps Engineer who takes initiative, identifies problems early, and drives end-to-end solutions to join our fully remote team and contribute to the growth and success of OpenSesame’s eLearning platform. You bring deep technical expertise in CI/CD pipelines, infrastructure automation, and cloud platforms, along with strong collaboration and communication skills. You design and manage scalable, secure systems primarily on AWS, leveraging Infrastructure as Code (IaC) to ensure high performance and resilience.

Success in this role requires strong ownership, technical leadership, and a proactive approach to improving systems and developer experience through automation, collaboration, and the thoughtful adoption of modern tooling, including AI-assisted workflows.

Performance Objectives

In your first 90 days:

Get fully integrated into the team’s workflow, integrate with the team, and begin contributing to secure, scalable infrastructure while identifying key opportunities to improve developer experience.

• Team Integration & Shared Ownership: Build strong relationships across our engineering teams. Gain an understanding of infrastructure workflows and shared responsibilities for security, and automation. Champion a culture of ownership across the full software development lifecycle.
• Technical Contribution: Enhance our Infrastructure Automation and cloud configuration, demonstrating expertise in IaC tools (e.g. Terraform) to enable consistent, auditable and automated infrastructure provisioning.
• Mentorship & Skill Development: Mentor engineers on DevOps principles including security by design, observability, and infrastructure automation. Share expertise in AWS, IaC, CI/CD, and security best practices. Foster a culture of continuous learning through peer reviews, knowledge sharing, and hands-on technical leadership.
• Improve Team Processes: Engage fully in the team's agile ceremonies, retrospectives, and discussions. Help evolve infrastructure and platform team practices such as automated testing for infrastructure, pipeline as code, and progressive delivery to improve feedback loops and system maintainability.
• AI & Automation Opportunities: Identify opportunities to reduce manual toil and improve developer workflows using automation and AI-assisted tooling; deliver at least one measurable improvement.

Within 6 months:

Lead infrastructure initiatives, improve developer experience, and serve as a key technical resource across teams. Elevate developer productivity through automation, tooling, and security enablement. Act as a technical resource for the team.

• Ownership: Fully own and improve key infrastructure components, such as IaC libraries, CI/CD pipelines, bootstrapping modules and monitoring tools. Identify and implement enhancements to security controls, reliability, observability, or cost-efficiency improvements within our AWS infrastructure stack.
• Developer Enablement in Practice: Introduce and refine internal tooling, templates, and scripts to eliminate friction in local development, and deployment. Establish self-service workflows that empower developers without compromising security.
• Lead by Example: Continue engaging in pair programming and mobbing to lead important initiatives w