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About the Role

League is seeking a Software Security Engineer to join our Security Engineering organization. This role focuses on building internal security tooling and security-by-design engineering capabilities across our healthcare platform ecosystem. It is a hands-on software engineering position focused on developing custom security infrastructure, developer security tooling, and automation systems to enhance platform security at scale. You will collaborate with Security, Platform Engineering, Infrastructure, and Product Engineering teams to create tools and workflows that improve secure software delivery, automate security operations, and protect sensitive data. This is not a governance, audit, or advisory-only role; we seek an engineer who writes production-quality code, builds scalable systems, and applies strong software engineering principles to solve complex security challenges in a modern cloud-native environment. As League scales AI-native healthcare experiences, security engineering is critical for ensuring our systems remain secure, resilient, compliant, and developer-friendly.

Responsibilities

Design, build, and maintain custom internal security tooling used across League’s 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.
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 League’s platform ecosystem.
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.
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.
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 efforts when required.
Ensure access management is performed in compliance with the employee's role and 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.

Requirements

5+ years of software engineering experience with strong focus on security engineering, platform engineering, or infrastructure security.
Experience building internal engineering or security tooling in cloud-native production environments.
Strong 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 working with AI-enabled systems, AI-assisted engineering workflows, or LLM-based applications is considered a strong asset.
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.

Skills

Security Engineering
Platform Engineering
Infrastructure Security
Backend Engineering
API Development
Automation Systems
Secure Authentication
Authorization Systems
CI/CD Integration
Developer Workflows
Kubernetes
Distributed Systems
AI-enabled Systems
AI-assisted Engineering
LLM Applications
Cloud-native Environments
AWS
GCP
Secrets Management
Identity Management
Vulnerability Detection
Remediation Automation
Policy Enforcement
Security Telemetry
OAuth/OIDC
RBAC
Service Authentication
Secure Session Handling
Container Security
Infrastructure Hardening
Observability
Monitoring
AI Fluency

Location

Toronto, Canada
US
Remote (Canada)
Remote (US)

Work Type

Full-time
Office-centric
Remote-eligible
Hybrid

Experience Level

5+ years of software engineering experience

Salary/Compensations

$159,100—$198,000 CAD

About the Company

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.
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.

Equal Opportunity

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.