Senior DevOps Software Engineer - Remote (Canada)

OpenSesame is a trusted partner for workforce reinvention in the age of AI, delivering integrated software and expert services. They are seeking a Senior DevOps Software Engineer to enhance their eLearning platform, focusing on infrastructure automation, cloud platforms, and improving developer experience through collaboration and modern tooling.

Responsibilities:

• 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
• 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
• Enhance our Infrastructure Automation and cloud configuration, demonstrating expertise in IaC tools (e.g. Terraform) to enable consistent, auditable and automated infrastructure provisioning
• 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
• 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
• Identify opportunities to reduce manual toil and improve developer workflows using automation and AI-assisted tooling; deliver at least one measurable improvement
• 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
• 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
• 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
• Continue engaging in pair programming and mobbing to lead important initiatives while fostering strong collaboration across the organization. Document and advocate for DevOps best practices across the engineering organization
• Help the team break down complex work into vertical slices, ensuring incremental value delivery and fast feedback loops
• Mentor engineers across teams and collaborate with engineering managers to help support hiring efforts in Mexico. Act as a connector between engineers, helping align best practices across teams
• Partner with engineering teams to document golden paths for infrastructure and deployment. Establish patterns and playbooks that support consistent, secure, and productive developer workflows
• Proactively identify and introduce improvements—including AI-assisted tools and automation—to reduce technical debt, improve system reliability, and enhance developer productivity
• Foster a culture where each team member feels empowered to take initiative and contribute to the success of the team. Encourage and create sustainable patterns and tooling that accelerate delivery without increasing risk
• Continue mentoring engineers at all levels, fostering a strong sense of collaboration and knowledge-sharing within both the Mexico team as it grows and the broader OpenSesame engineering team
• Work with engineering leadership to define and implement long-term technical strategies in infrastructure, security, developer enablement, and the responsible adoption of emerging technologies that align with our company and team goals
• Provide thoughtful input to engineering leadership on the needs, challenges, and opportunities of growing the engineering team in Mexico. Advocate for strategies that align with the team’s strengths and address gaps in skills or processes
• Continue leading efforts to retire legacy technologies and simplify architecture while ensuring the Drupal 7/Angular marketplace remains stable and well-supported

Requirements:

• Deep technical expertise in CI/CD pipelines
• Infrastructure automation experience
• Experience with cloud platforms, primarily AWS
• Strong collaboration and communication skills
• Experience with Infrastructure as Code (IaC)
• Ownership and technical leadership skills
• Proactive approach to improving systems and developer experience
• Mentorship experience in DevOps principles
• Experience with security best practices
• Experience with agile methodologies
• Ability to identify opportunities for automation and AI-assisted tooling
• Experience with IaC tools (e.g. Terraform)
• Ability to document and advocate for DevOps best practices
• Experience with modern technologies and tools
• Ability to mentor engineers across teams
• Experience in defining and implementing long-term technical strategies
• Ability to provide input to engineering leadership on team needs and challenges
• Experience in leading modernization efforts and retiring legacy technologies
• Experience with Terraform
• Experience with AWS
• Experience with Github Actions
• Experience with Docker
• Experience with Chef
• Experience with Python
• Experience with PHP
• Experience with Go
• Experience with C#