Principal Security Engineer

About League League is one of the fastest-growing technology companies in Canada and the leading healthcare experience platform. Getting healthcare is often the easy part — finishing it is where things fall apart: people book the appointment and skip the follow-up, fill the prescription and stop taking it, get the referral and never make the call. That gap costs health plans and health systems money, and it costs people their health. League closes that gap — identifying what each person needs to do next, clearing what’s in their way, and getting it done, for the 70 million+ people whose care already runs through our platform. Health plans and health systems trust us to do this at scale. Organizations like Manulife, SCAN, Geisinger, and Medibank on the payer side, and Baptist and Shoppers Drug Mart on the provider side.

Position Summary:

League is looking for a Principal Security Engineer to serve as the senior technical leader within our Security Engineering organization. This role entails designing and driving security architecture across a rapidly AI-native engineering environment, in close partnership with Product Security and Security Operations.

Product Security owns day-to-day security reviews and vulnerability management; Security Operations owns detection and response. This role sets technical direction and design for the organization's most complex and novel systems, including AI/agentic architectures, and serves as the connective tissue that makes the broader security function more effective.

The right person for this role doesn't wait for a ticket. They show up in design conversations, ask the right question at the right moment, and leave engineering and security colleagues alike more capable than they found them - all while being a strategic cross-functional partner that people enjoy collaborating with.

What you'll be doing:

• Design and implement security architecture and controls across encryption/key management, IAM, and core infrastructure
• Set technical direction and design for the organization's most complex and novel systems - including AI/agentic architectures, major platform changes, and novel integrations
• Partner proactively with engineering and product teams on secure-by-default design, embedding security capability directly into their workflows
• Provide technical mentorship to Security Software Engineering and to individuals within Product Security and Security Operations, raising technical capability across the broader security function
• Serve as senior technical escalation point and design advisor to Product Security and Security Operations on complex technical questions, without owning execution of their programs
• Set direction and design for security automation initiatives, partnering with Security Software Engineering, who owns implementation and build
• Translate technical risk into business terms for leadership, customers, and compliance stakeholders

What you'll bring to the team:

• 8+ years in security engineering, with demonstrated depth in at least two of: encryption/key management, IAM, cloud security architecture, application security
• Direct, hands-on experience securing AI-integrated systems including LLM applications, coding agents, or MCP-style tool integrations; not just familiarity with the concepts
• Experience operating in a regulated environment (HIPAA, HITRUST, SOC 2, PIPEDA, or equivalent), including translating compliance requirements into engineering practice
• Experience collaborating within a broader security organization (partnering with product/application security and security operations functions) rather than as a sole practitioner owning every function end-to-end
• Able to strategically influence across peer functions and ensure alignment to overall Security objectives
• Track record of influencing engineering decisions and behaviour without formal authority over the teams involved