Senior Software Security Engineer

About League

 

Founded in 2014, League is the leading healthcare consumer experience (CX) platform, powered by artificial intelligence (AI), reaching more than 63 million people around the world and delivering the highest level of personalization in the industry. Payers, providers, and consumer health partners build on League’s platform to deliver high-engagement healthcare solutions proven to improve health outcomes. League has raised over $285 million in venture capital funding to date, powering the digital experiences for some of healthcare’s most trusted brands, including Highmark Health, Manulife, Medibank, and Shoppers Drug Mart.

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

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  Design, build, and maintain custom internal security tooling used across League’s engineering organization



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  Develop automation systems that improve application security, secrets management, identity management, and secure software delivery workflows



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  Build developer-friendly security tooling integrated into CI/CD pipelines and internal engineering platforms



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  Create scalable systems for vulnerability detection, remediation automation, policy enforcement, and security telemetry collection

Secure Software Development

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  Write secure, maintainable, production-quality code across backend services, APIs, and cloud-native systems



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  Develop security services and APIs supporting authentication, authorization, secrets management, and access governance



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  Build and maintain tooling around OAuth/OIDC flows, token lifecycle management, RBAC, service authentication, and secure session handling



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  Improve secure-by-default engineering practices across League’s platform ecosystem

Cloud & Infrastructure Security

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  Build and automate cloud security controls across AWS, GCP, and Kubernetes environments



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  Develop tooling for infrastructure security, workload identity, encryption management, and runtime protection



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  Partner with Platform Engineering teams to strengthen container security, Kubernetes security posture, and infrastructure hardening



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  Improve observability and monitoring for security events, anomalous behavior, and operational risk

AI & Security Innovation

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  Build security capabilities that support AI-native engineering workflows and AI-powered healthcare experiences



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  Evaluate emerging AI-assisted security tooling and identify opportunities to improve engineering productivity and platform protection



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  Develop secure workflows and controls around AI-enabled systems and sensitive healthcare data usage

Cross-Functional Collaboration

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  Partner closely with Security, Infrastructure, Platform Engineering, Compliance, and Product Engineering teams to drive secure engineering practices



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  Translate security concepts into practical engineering solutions that improve developer experience and operational efficiency



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  Support security incident response, root cause analysis, and remediation efforts when required

What You Bring

• 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.

 

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

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

 

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

 

CANADA APPLICANTS ONLY: The Canada-specific compensation range below for this full-time position is exclusive of bonus, equity and benefits. This range reflects the minimum and maximum target for base salaries for the position across all Canadian locations. The salary range is intentional to account for the performance and career progressions a Leaguer will experience in the role throughout their time at League. Where in the band you may land is determined by job-related skills/experience. Your recruiter can share more about the specific salary range specific to your skills and experience during the hiring process.

Compensation range for Canada applicants only

$159,100 - $198,000 CAD

Our employees come from different backgrounds, and we celebrate those differences. We are looking for the best candidates for our open roles, but do not expect applicants to meet every qualification in order to be considered. If you are excited about what you could accomplish at League and believe you can add value to our team, we would love to hear from you.

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 View email address on jobs.jobcopilot.com .

Our Application Process:

 

Applying to a role you love can be exhausting, and understanding the next steps can feel vague and uncertain. You have done the hard part of submitting your application; let's do ours by sharing potential next steps

• You should receive a confirmation email after submitting your application.


• A recruiter (not a computer) reviews all applications at League.


• If we see alignment with League's needs, a recruiter will reach out to learn more about your goals. The recruiter will also share the team-specific interview process depending on the roles you are exploring.


• The final step is an offer, which we hope you will accept!


• Prior to joining us, we conduct reference and background checks. Additional checks could be required for US Candidates, depending on the role you are exploring.

Here are some additional resources to learn more about League:

Work Location:

We have a mix of office-centric roles based in our vibrant Toronto office, and remote-eligible roles based anywhere in Canada or US. Each job posting will indicate where the role will be based. Regardless of the role’s posted location, all Toronto-area Leaguers (living within 65 km of our downtown HQ) collaborate in-office Monday through Thursday. Depending on your distance to the office, you’ll enjoy 10 or 20 Flexible Remote Days each quarter for focus and deep-work time. We are committed to fostering a meaningful work environment and connections for all Leaguers regardless of location.

Recognize and Avoid Employment scams. Practice safe job searching.

Scammers are getting craftier and leveraging fake job postings to get personal information. Know the warning signs and protect yourself from scammers. Learn more here .

 

Use of AI Notice
We are committed to ensuring fairness and transparency throughout our hiring process. League may use Artificial Intelligence (AI) tools to assist in the screening of applicants for this position. Please check out our stance on using AI in recruitment here .

 

Review our for information on how League is protecting personal data.