ON - DevOPS/Cloud Engineer - Senior

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.
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.
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. 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.
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:
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. 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.
You will lead the adoption and operation of Docker and Kubernetes, ensuring resilient service deployment, scaling, and recovery.
Improve performance. 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.
You will bridge the gap between the cloud engineering team and the development teams, enabling faster and more reliable deployments. You will partner with developers, quality assurance, and operations teams to improve workflows, mentor junior engineers, and maintain clear runbooks and internal guides. You will participate in agile and sprint planning processes with the development teams and debug operational issues as they arise.
You may have worked in health technology and be familiar with electronic medical records, healthcare standards such as HL7 and FHIR, and compliance frameworks like ISO 27001, SOC 2, or PHIPA.
The technical experience. You are proficient in Infrastructure as Code with Terraform, and in building CI/CD pipelines using tools like GitHub Actions or Jenkins. You have hands-on expertise with containerization using Docker, and your cloud background is strongest in Azure, or with AWS and/or GCP. You bring solid development skills in Java, Bash, and Python, and experience working databases. You have implemented monitoring and logging with tools like Prometheus or Grafana and you stay ahead by leveraging AI tools for DevOps/DevSecOps.
The experience with AI-assisted DevOps. You are fluent in AI-assisted DevOps workflows and know how to responsibly incorporate AI-generated suggestions into infrastructure, monitoring, and deployment processes. You have integrated AI-assisted tools into your daily workflows to automate provisioning, enhance monitoring, minimize manual effort, and expedite deployment while maintaining responsible oversight. You understand both the capabilities and limitations of these tools.
You are motivated by technical challenges, enjoy modernizing legacy infrastructure, and are excited to work at the intersection of DevOps, cloud engineering, and AI-assisted automation.
You are an effective communicator and team player who fosters knowledge sharing, encourages feedback, and builds a high-performing DevOps culture. You have experience mentoring junior engineers and collaborating with developers, quality assurance, and operations teams to improve workflows and documentation.
Our team is dedicated to building resilient, compliant, and easy-to-use technology that transforms how care is delivered.
Transformation starts with a strong team.
Our workplace embraces diversity and prioritizes the well-being of our team and the communities we serve.
We offer a remote-first work environment, opportunities for growth within OSCAR Pro or across the broader WELL Health Technologies Group, and a supportive culture that balances professional success with personal well-being. Whether you are driving projects that shape the future of healthcare or focusing on your development, we are here to support you.
At OSCAR Pro, we are committed to fair and equitable compensation and aim to provide a competitive salary that reflects the value and expertise of the successful candidate.
A virtual interview with a Talent Advisor to discuss your experience and interest in the role. The conversation will be recorded using BrightHire, an AI-powered video interview tool. An at-home technical assessment.
A 2-hour virtual interview with the Director, Engineering and Director, IO of SRE & DevOps Enablement. This will be an opportunity for you to discuss your technical experience. A virtual interview with the VP, Technology.
We welcome and celebrate the diversity of applicants and team members across ability, race, gender identity, sexual orientation, and perspective. Accommodations are available on request for candidates taking part in all aspects of the selection process.

• LI-Remote