Senior Devops Engineer

Description:

OSCAR Pro, a premier Electronic Medical Records (EMR) platform in Canada and a member of the WELL Health Technologies family, is seeking a highly skilled Senior DevOps Engineer to join its team. Originally developed by McMaster University’s Department of Family Medicine, OSCAR Pro has evolved into one of the most trusted EMR solutions in Canada, designed to enhance healthcare delivery and improve patient outcomes.

The Senior DevOps Engineer will play a pivotal role in transforming OSCAR Pro’s infrastructure, modernizing its core systems, and integrating AI-assisted automation tools to drive efficiency, scalability, and innovation across the platform. This position offers a unique opportunity to directly impact the future of digital healthcare delivery while contributing to a high-performing technology team serving clinics nationwide.

This role is fully remote, with the option to work hybrid from Toronto or Vancouver.

Key Responsibilities:

• Automate Infrastructure:
  Design, automate, and maintain infrastructure systems using Terraform, Ansible, GitHub Actions, and Jenkins, enabling secure and scalable CI/CD pipelines for continuous software delivery.

• Integrate AI in DevOps:
  Incorporate AI-assisted tools (e.g., Claude Code, Copilot) to automate repetitive tasks, optimize system monitoring, and accelerate deployment and incident response processes.

• Containerization & Orchestration:
  Lead the adoption of Docker and Kubernetes for resilient service deployment, fault tolerance, scaling, and self-healing infrastructure management.

• Performance & Monitoring:
  Implement Prometheus, Grafana, ELK/EFK stacks, and other observability tools to improve monitoring, alerting, and overall infrastructure reliability.

• Optimize DevOps KPIs:
  Establish and monitor key DevOps performance metrics—deployment frequency, lead time for changes, and change failure rate—to continuously improve delivery pipelines and operational excellence.

• Enhance Security (DevSecOps):
  Embed DevSecOps practices, manage secrets securely, implement robust identity and access management (IAM/RBAC), and ensure compliance with industry standards.

• Collaboration & Leadership:
  Bridge the gap between cloud engineering, development, QA, and operations teams, mentoring junior engineers and fostering a collaborative DevOps culture.

• Continuous Improvement:
  Modernize legacy systems through automation and cloud-native solutions, optimizing efficiency and reliability across all technical operations.

Qualifications and Requirements:

• Education:
  Bachelor’s degree in Computer Science, Information Technology, Software Engineering, or related field.

• Technical Experience:

  • Strong hands-on experience with Terraform, GitHub Actions, Jenkins, Ansible, and Docker/Kubernetes.

  • Expertise in cloud platforms, particularly Microsoft Azure (experience with AWS or GCP is a plus).

  • Proficient in Java, Bash, and Python scripting.

  • Experience managing databases and implementing secure, compliant infrastructure environments.

  • Familiarity with AI-assisted DevOps tools and responsible use of generative AI technologies in deployment pipelines.

  • Knowledge of DevSecOps principles, including TLS, IAM, RBAC, and secret management.

• Preferred Industry Knowledge:

  • Experience in healthcare technology or EMR systems.

  • Understanding of HL7, FHIR, ISO 27001, SOC 2, or PHIPA compliance frameworks.

• Soft Skills:

  • Strong analytical and troubleshooting capabilities.

  • Excellent communication and collaboration skills across multidisciplinary teams.

  • Leadership experience and ability to mentor team members.

  • Self-driven, innovative, and comfortable with ownership of complex systems.

Why Join OSCAR Pro:

• Meaningful Impact:
  Contribute to a mission-driven platform improving healthcare outcomes for millions of Canadians.

• Technical Challenges:
  Work on cutting-edge DevOps modernization initiatives involving AI integration, cloud scalability, and multi-tenant architectures.

• Career Growth:
  Opportunity to lead a small DevOps team or progress into senior principal-level technical roles within WELL Health Technologies.

• Work Flexibility:
  Enjoy a remote-first environment with optional hybrid locations in Toronto and Vancouver.

Interview Process:

1. Virtual Interview with Talent Advisor (recorded using BrightHire).

2. Technical Assessment (at-home exercise).

3. 2-Hour Technical Interview with Director of Engineering and Director of SRE & DevOps Enablement.

4. Discussion with VP of Technology.

5. Meet and Greet with the Engineering Team.