Founded in 2014, League is the leading healthcare consumer experience (CX) platform powered by artificial intelligence (AI) that serves more than 63 million people worldwide. It partners with payers, providers and consumer‑health brands to deliver highly engaging, personalized digital experiences.

Position Summary

League is hiring a Software Security Engineer to build internal security tooling and security‑by‑design capabilities across our healthcare platform ecosystem. The role is a hands‑on software engineering position that focuses on developing custom security infrastructure, developer security tooling, and automation systems to strengthen League’s platform security posture at scale.

What You Will Do

Security Tooling & Platform Engineering

- Design, build, and maintain custom internal security tooling used across the engineering organization
- Develop automation systems that improve application security, secrets management, identity management, and secure software delivery workflows
- Build developer‑friendly security tooling integrated into CI/CD pipelines and internal engineering platforms
- Create scalable systems for vulnerability detection, remediation automation, policy enforcement, and security telemetry collection

Secure Software Development

- Write secure, maintainable, production‑quality code across backend services, APIs, and cloud‑native systems
- Develop security services and APIs supporting authentication, authorization, secrets management, and access governance
- Build and maintain tooling around OAuth/OIDC flows, token lifecycle management, RBAC, service authentication, and secure session handling




- Improve secure‑by‑default engineering practices across the platform ecosystem

Cloud & Infrastructure Security

- Build and automate cloud security controls across AWS, GCP, and Kubernetes environments
- Develop tooling for infrastructure security, workload identity, encryption management, and runtime protection
- Partner with Platform Engineering teams to strengthen container security, Kubernetes security posture, and infrastructure hardening
- Improve observability and monitoring for security events, anomalous behavior, and operational risk

AI & Security Innovation

- Build security capabilities that support AI‑native engineering workflows and AI‑powered healthcare experiences
- Evaluate emerging AI‑assisted security tooling and identify opportunities to improve engineering productivity and platform protection
- Develop secure workflows and controls around AI‑enabled systems and sensitive healthcare data usage

Cross‑Functional Collaboration

- Partner closely with Security, Infrastructure, Platform Engineering, Compliance, and Product Engineering teams to drive secure engineering practices
- Translate security concepts into practical engineering solutions that improve developer experience and operational efficiency
- Support security incident response, root cause analysis, and remediation when required

What You Bring





- 5+ years of software engineering experience with a strong focus on security engineering, platform engineering, or infrastructure security
- Experience building internal engineering or security tooling in cloud‑native production environments
- Solid hands‑on backend engineering experience building APIs, services, and automation systems
- Experience implementing secure authentication and authorization systems in production applications
- Experience working in regulated or high‑trust environments such as healthcare, fintech, or enterprise SaaS is strongly preferred
- Experience integrating security tooling into CI/CD pipelines and developer workflows
- Experience working with Kubernetes and distributed systems in production environments
- Experience with AI‑enabled systems, AI‑assisted engineering workflows, or LLM‑based applications is a strong asset

Security‑Related Responsibilities

- Ensure access management is performed in compliance with employee roles and responsibilities
- Execute League policies and procedures within the department/team
- Notify HR, Legal, Compliance & Security of any incidents, breaches or policy violations
- Comply with Information Security Policies

Compensation (Canada only)

$159,100–$198,000 CAD per year (baseline salary; excludes bonus, equity and benefits)

Equal Employment Opportunity

League is 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 need assistance during our recruitment process, please contact

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📌 Senior Software Security Engineer (Toronto)
🏢 League
📍 Toronto