Senior DevOps Engineer

Who we are

OSCAR Pro, a leading Electronic Medical Records (EMR) platform in Canada, is part of the WELL Health Technologies family. Initially developed by McMaster University's Department of Family Medicine, OSCAR Pro was built on a foundation of collaboration to improve healthcare delivery and patient outcomes. We have integrated innovations from various OSCAR service providers to offer a robust, secure, and versatile solution tailored to the diverse needs of clinics of all sizes.

Our platform empowers healthcare providers by streamlining administrative tasks, enhancing clinic efficiency, and enabling more time for patient care. With features like digital patient engagement, secure messaging, and seamless integration with other healthcare systems, OSCAR Pro reduces the administrative burden on clinics and improves the overall patient experience.

Our mission is to empower practitioners to deliver high-quality care while spending less time on administration. By providing cutting-edge digital tools, we ensure that healthcare professionals can focus on what truly matters—improving patient outcomes and experiences.

Who we need

We are looking for a Senior DevOps Engineer who is passionate about creating high-performing, reliable, and scalable infrastructure that directly improves healthcare outcomes for Canadians. In this role, you will work on the OSCAR Pro platform, a critical electronic medical record system, and help modernize its infrastructure while integrating AI-assisted tools to optimize software delivery.

You will play a central role in enabling development teams to deliver faster and more reliably, driving measurable improvements in deployment frequency, lead time for changes, and change failure rates. You will adopt cutting-edge DevOps practices, including containerization and orchestration, while collaborating with teams across cloud engineering, development, quality assurance, and operations.

This job posting is for existing vacancy that is a remote first opportunity, with hybrid options available in Toronto and Vancouver if desired.

What is in it for you

Impact. You will play a central role in building and scaling OSCAR Pro DevOps pipelines and infrastructure to ensure secure, reliable, and high-velocity software delivery. You will make a meaningful impact on the performance and reliability of the OSCAR healthcare platform, as well as the lives of healthcare users. Your work will directly improve developer productivity, system reliability, and ultimately patient care.

Technical challenges. You will drive modernization initiatives across OSCAR infrastructure, adopting multi-tenancy, containerization, and AI-assisted automation to optimize continuous integration and continuous deployment workflows. You will gain exposure to cutting-edge healthcare DevOps practices, AI-assisted automation, and system architecture while contributing to a new platform that offers challenging and rewarding technical work.

Career growth. You will join the largest owner and operator of outpatient medical clinics in Canada, contributing to a mission-critical technology platform with long-term growth potential. There may be opportunities to lead a small team focused on DevOps and the technical aspects of development, or to grow into a senior principal-level technical role.

As our new Senior DevOps Engineer, you will focus on:

Automate infrastructure. You will design, automate, and maintain infrastructure systems, as well as continuous integration and continuous deployment pipelines, using Terraform, Ansible, GitHub Actions, and Jenkins to ensure secure, scalable, and high-quality software delivery. You will automate and streamline operations tasks to free up the infrastructure and operations team to focus on enabling the development teams. Enhance DevOps with AI. You will integrate artificial intelligence-assisted tools such as Claude Code or Copilot to automate repetitive tasks, improve monitoring, enhance reliability, and accelerate deployment processes. Leverage containerization and orchestration. You will lead the adoption and operation of Docker and Kubernetes, ensuring resilient service deployment, scaling, and recovery. Improve performance. You will implement Prometheus, Grafana, ELK, or EFK stacks, along with Application Insights and Log Analytics, to enhance system observability, minimize downtime, and facilitate rapid incident response. Measure. You will track and improve key DevOps metrics such as deployment frequency, lead time for changes, and change failure rate. You will establish the right metrics and dashboards to monitor these KPIs, and work to increase deployment frequency from monthly to weekly or daily while reducing the change failure rate. Optimize. You will embed DevSecOps practices across all workflows, manage secrets securely, and maintain a ready infrastructure. You will enhance monitoring and logging for observability, reduce critical system issues, and streamline incident management