Senior DevOps Software Engineer - Remote (Canada)

About OpenSesame

OpenSesame is transforming workforce development with an AI-powered marketplace of 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 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 while fostering strong collaboration across the organization. Document and advocate for DevOps best practices across the engineering organization.
• 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 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.
• Enablement & Standards: Partner with engineering teams to document golden paths for infrastructure and deployment. Establish patterns and playbooks that support consistent, secure, and productive developer workflows.
• Evaluate and adopt modern technologies: Proactively identify and introduce improvements-including AI-assisted tools and automation-to reduce technical debt, improve system reliability, and enhance developer productivity.

By the end of your first year:

Establish yourself as a technical leader and mentor, driving long-term improvements in productivity, platform reliability, and operational safety and helping shape OpenSesame’s engineering presence while driving technical excellence.

• Promote Team Ownership: 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.
• Mentor & Develop Peers: 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.
• Help Shape Team Strategy: 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.
• Advise Management: 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.
• Drive Modernization Efforts: Continue leading efforts to retire legacy technologies and simplify architecture while ensuring the Drupal 7/Angular marketplace remains stable and well-supported.

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
• Github Actions
• Docker
• Chef
• Python
• Docker
• PHP
• Go
• C#

Location: This is a remote-first role based in Canada. 

Performance Driven: We're looking for self-starters with a track record of delivering excellent results, and 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.

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.

Location: This is a remote-first role based in Canada. 

Performance Driven: We're looking for self-starters with a track record of delivering excellent results, and 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.

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.