League is one of the fastest-growing technology companies in Canada and the leading healthcare experience platform. 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's security engineering team is responsible for scaling security across the development lifecycle. We believe in security by design and follow a paved-road philosophy: we build or buy tooling that integrates into our platform so it is easier for engineers to do the right thing than the wrong thing. Security is everyone's responsibility, and security engineering is how we make it possible for engineers to ship high-quality code to production several times a day with security built in.

This role is an intermediate security engineer who splits their time between engagement work and engineering work. On the engagement side you will run security reviews for new product work, contribute to technical deep dives on existing systems, assess vendors before they are approved for use, and review third-party vendors that handle League customer data. On the engineering side you will write code and engage with tooling and systems: automation that removes manual review steps, checks that run in our pipelines, and tooling that makes findings easier to route, track and close.

League ships AI-enabled features and our engineers work with AI-assisted development tooling daily. Reviewing those systems, and reasoning about the security of code and fixes that AI produces, is a standing part of this role rather than a specialty. You will bring some experience with threat modeling and cloud architecture to meaningfully contribute to secure design practices, while senior engineers and architects own the broader security strategy.

You think in systems and processes, which is how you will find the second-order, long-term fix rather than the quick, most immediate one. You share what you learn, and you can explain risk clearly to a software engineer and to infrastructure leadership in the same week. We welcome new ideas and encourage diverse experience, in every meaning of the word - if you have a unique background, deep interests in a niche topic of security or engineering, or some experience that brings new approaches to security and engineering, this is a strength that we welcome on the team.

While this summary outlines the main job responsibilities, it is by no means exhaustive - we are a rapid-moving organization, and change can happen quickly here, especially when it raises the bar of security for League and our customers. Conduct security reviews of product features, integrations, and platform changes, documenting resulting security requirements Participate in threat modeling exercises to identify risks in system design and data flow Perform security assessments of applications, APIs, and cloud configuration, and provide remediation guidance engineering teams can act on Review AI-enabled product features for prompt injection,



excessive agency and unintended exposure of member data Triage and score security findings, and drive remediation with the owning teams Own the configuration, tuning, and triage workflow for security tooling Automate manual review efforts and embed security checks into the SDLC Build training materials and documentation on secure coding practices and common vulnerabilities; Support League’s shift left by contributing reusable security controls to our paved road so that common vulnerabilities are prevented by default Contribute to the development and maintenance of League’s security standards and internal documentation. Conduct security reviews of third-party vendors that process or store League data, and support customer security assurance requests.

Support SOC 2 Type II, HITRUST, HIPAA, and PHIPA control design, testing, and evidence gathering in partnership with the Privacy and Compliance team. Communicate risk findings clearly to different audiences, adapting language and level of detail for engineers versus leadership. 2+ years of professional experience in application or product security, or in software engineering with substantial security responsibility ~ Ability to find what scanners miss: broken access control, tenant isolation failures, business logic flaws ~ Working knowledge of authentication and authorization in modern applications, including OAUTH 2.0 / OIDC, session and token handling, and role or attribute-based access control ~ Familiarity with CI / CD and software supply chain security, including pipeline-integrated testing, dependency management, and secrets handling ~ Solid working knowledge of common application vulnerabilities (e.g., Experience with AI and LLM application security, including prompt injection, agentic tool-use risk and retrieval pipeline exposure ~ Some exposure to cloud security concepts and secure cloud architecture, ideally GCP, including containerized workloads. ~ A track record of writing and shipping code other people rely on, in Python, Go, or a comparable language ~ Experience handling PHI or comparably sensitive data in a regulated environment. Self-driven security work: side projects, CTFs, published research, or a coordinated disclosure history Security-Related Responsibilities Responsibility and accountability for executing League's policies and procedures within the department/ team Notification of HR, Legal, Compliance & Security of any incidents, breaches or policy violations Compliance with Information Security Policies CANADA APPLICANTS ONLY:



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

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. 109,100 - $136,400 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. 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 Individual Contributors: Use AI to improve personal productivity and quality of output Senior ICs / Managers: Integrate AI into team workflows and improve processes Drive AI adoption at the organizational level and shape how work is done across teams Demonstrated experience using AI tools in a practical, responsible way Ability to balance efficiency with quality and sound judgment 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 .

We have a mix of office-centric roles based in our vibrant Toronto office, and remote-eligible roles based anywhere in Canada or US. 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 have a mix of office-centric roles based in our vibrant Toronto office, and remote-eligible roles based anywhere in Canada or US. 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.

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📌 Security Engineer - Junior (Toronto)
🏢 League
📍 Toronto