Principal, Security Engineer

League Inc.•Toronto, ON

1d•CA$220,000 - CA$280,000•Hybrid

About The Position

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.

Requirements

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

Responsibilities

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