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

CANADA APPLICANTS ONLY: The Canada-specific compensation range below for this full-time position is exclusive of bonus, equity and benefits. This range reflects the minimum and maximum target for base salaries for the position across all Canadian locations. The salary range is intentional to account for the performance and career progressions a Leaguer will experience in the role throughout their time at League. Where in the band you may land is determined by job-related skills/experience. Your recruiter can share more about the specific salary range specific to your skills and experience during the hiring process.

Compensation range for Canada applicants only

$220,000—$280,000 CAD

AI Fluency & Ways of Working

At League, we are an AI-native organization. We expect all employees regardless of role or level to thoughtfully leverage AI to improve the quality, speed, and impact of their work.

What this means in practice:

Use AI tools as part of your daily workflow to enhance productivity, problem-solving, and decision-making (e.g., drafting, analysis, coding, research, or process automation)
Apply judgment and accountability when using AI by reviewing outputs for accuracy, bias, and quality before use
Continuously learn and adapt as new AI tools and capabilities emerge, incorporating them into your ways of working
Identify opportunities to improve how work gets done from personal productivity to team-level workflows by leveraging AI effectively
Operate with strong data responsibility and security awareness, especially when working with sensitive or regulated information

How this scales by level:

Individual Contributors: Use AI to improve personal productivity and quality of output
Senior ICs / Managers: Integrate AI into team workflows and improve processes
Leaders: Drive AI adoption at the organizational level and shape how work is done across teams

What we look for:

Demonstrated experience using AI tools in a practical, responsible way
Curiosity and openness to experimenting with new technologies
Ability to balance efficiency with quality and sound judgment

Our employees come from different backgrounds, and we celebrate those differences. We are looking for the best candidates for our open roles, but do not expect applicants to meet every qualification in order to be considered. If you are excited about what you could accomplish at League and believe you can add value to our team, we would love to hear from you.

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. If you are an individual in need of assistance at any time during our recruitment process, please contact us at recruitinginfo@league.com.

Our Application Process:

Applying to a role you love can be exhausting, and understanding the next steps can feel vague and uncertain. You have done the hard part of submitting your application; let's do ours by sharing potential next steps

You should receive a confirmation email after submitting your application.
A recruiter (not a computer) reviews all applications at League.
If we see alignment with League's needs, a recruiter will reach out to learn more about your goals. The recruiter will also share the team-specific interview process depending on the roles you are exploring.
The final step is an offer, which we hope you will accept!
Prior to joining us, we conduct reference and background checks. Additional checks could be required for US Candidates, depending on the role you are exploring.

Here are some additional resources to learn more about League:

Work Location:

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.

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Use of AI Notice
We are committed to ensuring fairness and transparency throughout our hiring process. 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.

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Principal Security Engineer

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