Job Summary
DevOps Engineer
Pillway
Full-time
In-Office | Brampton, ON, Canada
Ignite Your Career: DevSecOps Engineer at Pillway
Location: Brampton, ON (In-Office)
Department: IT / Engineering
Reports To: Head of IT
About Pillway:
Pillway is a dynamic digital health company, not just a pharmacy. We are revolutionizing how millions of Canadians manage their health by merging cutting-edge technology, streamlined delivery, and truly patient-first care. As we scale, our technology team is the backbone, and we are laser-focused on building a platform defined by unshakeable security, massive scalability, and ultimate reliability. Join us to make a real-world impact that matters.
The Mission: Secure Innovation at Speed:
We are hunting for an exceptional DevOps Engineer—a security champion ready to embed protection across every line of code and every piece of infrastructure. This is your chance to own the security roadmap for a hyper growth healthcare platform. You'll ensure our cloud ecosystem is hardened against threats while keeping us compliant with critical regulations (PHIPA, PIPEDA, SOC 2). If you have a passion for cloud security, CI/CD automation, and enabling secure development in a fast-paced environment, this is your next challenge.
The DevOps Engineer will own DevOps and security engineering for our cloud platform. This includes hardening Azure, embedding security into every pipeline, and maintaining compliance with PHIPA, PIPEDA, and SOC 2. The role works closely with engineering, QA, and operations to make secure deployment the default rather than an afterthought.
This is a hands-on, end-to-end position with full ownership over a platform that patients depend on, including the autonomy to shape how we build, deploy, and secure it.
Cloud and infrastructure
Own Azure end-to-end, including networking (VPNs, VNets, NSGs, firewalls), VMs, databases, backups, and disaster recovery.
Build and maintain infrastructure as code using Terraform & Azure Kubernetes Cluster.
Plan and execute upgrades, patching, and capacity planning.
Support hybrid cloud and on-premises networking in coordination with internal and external teams.
CI/CD and developer enablement
Design and maintain secure CI/CD pipelines using Azure DevOps or similar tooling.
Integrate SAST, DAST, dependency scanning, and secrets detection into the build process.
Manage container and orchestration tooling, including Docker and Kubernetes.
Security operations
Own monitoring and incident response across the platform.
Triage and respond to alerts from SIEM, IDS/IPS, and MDR systems.
Lead investigations, remediation, and post-incident reviews.
Risk, identity, and data
Operate the vulnerability management program, including scanning, prioritization, remediation, and reporting.
Lead annual penetration tests and ensure findings are resolved within agreed SLAs.
Own IAM, Azure RBAC, and least-privilege enforcement.
Manage keys, secrets, certificates, and rotation policies.
Compliance and governance
Maintain our security and compliance posture for PHIPA, PIPEDA, and SOC 2.
Support internal and external audits.
Drive continuous compliance through automation and monitoring.
Four or more years of experience in DevOps or security engineering, with at least two years in a DevOps-focused role.
Bachelor's degree in Computer Science, Engineering, or equivalent practical experience.
Demonstrated hands-on experience with Azure services, security policies, and monitoring tools.
Strong proficiency in at least one IaC tool, such as Terraform, AKS.
Working knowledge of NIST, CIS Benchmarks, and OWASP.
Experience with Docker, Kubernetes, and modern CI/CD tooling.
Strong written and verbal communication skills, with the ability to collaborate effectively across engineering, security, and operations.
AZ-500, CISSP, CISM, or DevOps-focused certifications.
Experience in regulated healthcare environments (PHIPA, PIPEDA, SOC 2).
Hands-on experience with secrets management platforms such as HashiCorp Vault or Azure Key Vault.
Familiarity with generative AI security principles and emerging automation tools.
What We Offer: Built for Growth
A competitive compensation package designed to reward top talent.
Comprehensive health and dental benefits.
The rare opportunity to drive meaningful healthcare innovation across Canada.
A collaborative, fast-paced culture where every new idea is celebrated and accelerated.
Pillway is an inclusive employer and provides accommodations for applicants with disabilities throughout the recruitment process. Please let us know if you require accommodation.
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