Senior Software Security Engineer

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 seeking a Software Security Engineer to join our Security Engineering org and focus full-time on building internal security tooling and security-by-design engineering capabilities across our healthcare platform ecosystem. This is a highly hands-on software engineering role focused on developing custom security infrastructure, developer security tooling, and automation systems that strengthen League’s platform security posture at scale. You will work closely with Security, Platform Engineering, Infrastructure, and Product Engineering teams to build tools and workflows that improve secure software delivery, automate security operations, and protect sensitive healthcare and member data.

This is not a governance, audit, or advisory-only role. We are looking for 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 continues scaling AI-native healthcare experiences and enterprise platform capabilities, security engineering plays a critical role in ensuring our systems remain secure, resilient, compliant, and developer-friendly.

What You Will Do

: Security Tooling Platform Engineering 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 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 League’s 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,