League Inc.

Principal Security Engineer

Toronto, Canada · Principal · Full-time

Sponsorship not specified$220k-$280kDetected 5 days ago

GCPLLMsCybersecuritySOC OperationsComplianceHRISHIPAALeadershipMentoring

About the role

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.
The right person for this role doesn't wait for a ticket.

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
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

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Use of AI Notice
League may use Artificial Intelligence (AI) tools to assist in the screening of applicants for this position.
Please check out our stance on using AI in recruitment here.

CANADA APPLICANTS ONLY: The Canada-specific compensation range below for this full-time position is exclusive of bonus, equity and benefits.

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.
Health plans and health systems trust us to do this at scale.
League raises $95 million USD in Series C to build world's leading healthcare CX platform
We are committed to equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or Veteran status.
Highmark Health, Google Cloud, League: new digital front door to seamless care
Forbes x League: The Platformization Of Healthcare Is Here
Depending on your distance to the office, you'll enjoy 10 or 20 Flexible Remote Days each quarter for focus and deep-work time.

If we want better innovations in healthtech, we need more competition
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
Translate technical risk into business terms for leadership, customers, and compliance stakeholders
You have done the hard part of submitting your application; let's do ours by sharing potential next steps
We are committed to fostering a meaningful work environment and connections for all Leaguers regardless of location.
We are committed to ensuring fairness and transparency throughout our hiring process.

al employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or Veteran status

This listing is sourced directly from League Inc.'s careers page and normalized into a canonical job model.