Senior Software Security Engineer, League
CA$159.1-198k
The Canada-specific compensation range for this full-time position is exclusive of bonus, equity and benefits
Consumer experience platform for healthcare
Posted today
Consumer experience platform for healthcare
501-1000 employees
Posted today
CA$159.1-198k
The Canada-specific compensation range for this full-time position is exclusive of bonus, equity and benefits
501-1000 employees
Company mission
To power next-generation healthcare experiences with a platform built to enable CX transformation.
Role
Who you are
- 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
- 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
- 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
What the job involves
- 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
- 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
- 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, 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
- 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
- Security-Related Responsibilities:
- 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
Our take
Health benefits are a top requirement for anyone seeking a new job in the US today, but classic one-size-fits-all plans are no longer regarded fit for service. League's platform - for payers, providers, consumer health businesses, and employees - connects all benefits in one HIPAA-compliant place, to enable all bodies involved with health benefits to provide better customer healthcare experiences.
League is already one of the bigger players in the employee wellness space, having capitalised on the recently accepted correlation between employee health and productivity to secure huge clients like Uber, Shopify and Unilever. The company has seen significant investment, which will support the scaling of its platform-as-a-service offering. With more than 63 million contracted users, it is securing its position as the leading digital infrastructure for an integrated health ecosystem.
Freddie
Company Specialist at Welcome to the Jungle
Insights
-4% employee growth in 12 months
Company
Funding (last 2 of 4 rounds)
Feb 2022
$95m
SERIES C
Jul 2018
$47.1m
SERIES B
Total funding: $171.1m
Company benefits
- Flexible medical and dental plans
- 401(k) and RRSP matching programs
- Health, lifestyle, learning and family spending accounts
- Employee stock option program (ESOP)
- Generous leaves (including parental and sabbatical)
- Flexible time off
Company HQ
Entertainment District, Toronto, ON
Leadership
Michael Serbinis
(Founder & CEO)Founder of DocSpace and Kobo. Experience as CEO for Three Angels Capital and Board Director for Vector Insitute, among other prominent business leadership roles.
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