About LeagueFounded in 2014, League is the leading healthcare consumer experience (CX) platform, powered by artificial intelligence (AI). We reach more than 63 million people worldwide and deliver the highest level of personalization in the industry.Position SummaryLeague’s security engineering teams scale security throughout the development lifecycle and vulnerability management. As a Staff Security Engineer, you will be a principal technical leader who designs the long‑term security architecture and strategy across the platform, infrastructure, and engineering organization. You will move beyond incremental improvement to solve the highest‑impact, most ambiguous, and most foundational security problems.About The RoleArchitectural Leadership: Define and champion the long‑term technical security roadmap, architecture patterns, and standards for League’s applications, infrastructure, and multi‑cloud workplace.Cross‑Functional Strategy: Act as the primary security technical partner to Platform, Product, and executive leadership, driving alignment on multi‑quarter security initiatives.Security Design Governance: Lead high‑stakes, complex security design and architecture reviews (STRIDE/threat modeling) for new services and core platform migrations.Risk & Vulnerability Strategy: Design, implement, and automate organization‑wide frameworks for continuous vulnerability management and detection.Due Diligence Expertise: Architect the security due diligence program for critical third‑party vendors and partnerships handling sensitive customer data.Mentorship & Elevation:



Mentor senior and mid‑level security engineers, fostering a culture of security architecture excellence and technical leadership.About You8+ years of progressive security engineering experience, with at least 2 years at the senior or principal level.Deep expertise in cloud security architecture (AWS, GCP, or Azure) focusing on containerization (Kubernetes), cloud IAM, and infrastructure as code (Terraform).Proven track record of delivering large‑scale, cross‑organizational security initiatives from concept through production deployment.Ability to write secure, production‑grade code in Python, Go, Java, or TypeScript to build automation tools and scalable security services.Experience designing and implementing controls to achieve and maintain compliance with HIPAA or HITRUST.Mastery of application security, SDLC integration, authentication/authorization protocols (OAuth, OIDC), and common attack vectors.AI Fluency & Ways of WorkingUse AI tools daily to enhance productivity, problem‑solving, and decision‑making (e.G., drafting, analysis, coding, research).Apply judgment and accountability by reviewing AI outputs for accuracy, bias,



and quality.Continuously learn and adapt as new AI tools emerge, incorporating them into work processes.Identify opportunities to improve workflows at personal and team levels using AI.Operate with strong data responsibility and security awareness, especially with regulated information.What We Look ForDemonstrated experience using AI tools responsibly.Curiosity and openness to experimenting with new technologies.Ability to balance efficiency with quality and sound judgment.Security‑Related ResponsibilitiesEnsure access management complies with employee roles and responsibilities.Accountable for executing League’s policies and procedures within the department/team.Notify HR, Legal, Compliance, and Security of incidents, breaches, or policy violations.Comply with Information Security Policies.Salary InformationCanada applicants only: $199,000—$240,000 CAD (base salary range, exclusive of bonus, equity and benefits).Work LocationLeagues offers remote‑eligible roles based anywhere in Canada or the US. Office‑centric roles are based in Toronto. All Toronto‑area Leaguers collaborate in‑office Monday through Thursday, with flexible remote days each quarter.Equal Employment OpportunityWe 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 need assistance during the recruitment process, contact [email protected].#J-18808-Ljbffr

📌 Staff Security Engineer - C$199,000 - C$240,000 A Year (Winnipeg)
🏢 League
📍 Winnipeg