Principal Security Engineer

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.

• →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

• 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

We have a mix of office-centric roles based in our vibrant Toronto office, and remote-eligible roles based anywhere in Canada or US. Each job posting will indicate where the role will be based. Regardless of the role’s posted location, all Toronto-area Leaguers (living within 65 km of our downtown HQ) collaborate in-office Monday through Thursday. Depending on your distance to the office, you’ll enjoy 10 or 20 Flexible Remote Days each quarter for focus and deep-work time. We are committed to fostering a meaningful work environment and connections for all Leaguers regardless of location.