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 Build & Release Engineer to join our team. This role sits at the intersection of CI/CD infrastructure, release automation, and developer experience, with a strong emphasis on leveraging AI to scale engineering systems and workflows.

You will own and evolve the systems that power how software is built, tested, and released across League’s platform spanning web, mobile (iOS/Android), and backend services. You will design reliable, scalable, and AI-augmented build and release pipelines that enable teams to ship faster with confidence.

This role combines hands-on engineering, operational excellence, and AI-driven innovation to improve delivery velocity, reliability, and developer productivity across the organization.

In this role, you will:

Build & Release Systems

Design, maintain, and evolve automated build, packaging, and release workflows across web, backend, and mobile platforms
Own the end-to-end release lifecycle, including versioning, promotion, rollback, and hotfix strategies
Ensure high reliability and uptime of CI/CD systems through monitoring, alerting, and incident response
Support engineering teams in landing critical releases and resolving build or deployment issues

CI/CD Infrastructure & Optimization

Build and optimize CI/CD pipelines using modern tooling (e.g., GitHub Actions, CircleCI, self-hosted runners)
Improve build performance, cost efficiency, and execution times across pipelines
Manage and evolve containerized build environments (Docker) and Kubernetes-based infrastructure
Implement infrastructure-as-code practices (e.g., Terraform) for reproducible build environments

AI-Native Engineering & Automation (Core Competency)

Design and implement AI-assisted workflows to:

Automate release validation, failure triage, and incident analysis
Optimize pipeline performance and identify bottlenecks
Generate and maintain build scripts, configs, and test scaffolding

Build AI-powered tooling (agents, bots, or copilots) to support:

Release orchestration
Developer self-service workflows
CI/CD diagnostics and recommendations

Integrate AI into developer workflows to reduce manual effort and improve productivity
Continuously evaluate and adopt new AI tools and patterns to evolve League’s delivery capabilities

Developer Experience & Tooling

Build and maintain internal tools, dashboards, and CLI utilities to improve developer workflows
Enhance observability of build and release systems (logs, metrics, alerts)
Create and maintain documentation and self-service tooling for engineering teams
Partner with developers to understand friction points and improve release experience at scale

Security, Compliance & Platform Reliability

Implement and maintain secure build and release practices, including:

Certificate management
Secrets management
Compliance with platform and security standards

Partner with Security and Platform teams to ensure safe and compliant releases
Improve reliability through incident management, postmortems, and continuous improvement loops

About You:

3+ years experience in build/release engineering, DevOps, or platform engineering
Strong experience with CI/CD systems (e.g., GitHub Actions, CircleCI, Jenkins)
Proficiency with cloud platforms (GCP preferred, AWS/Azure acceptable)
Experience with containerization and orchestration (Docker, Kubernetes)
Strong programming skills (e.g., Go, Python, Java, or similar)

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

What We Offer

Comprehensive Health Benefits: We prioritize your well-being with complete medical, dental, and vision coverage
Bonus Program: Be rewarded for your contributions with our performance-based bonus program
Employee Stock Option Program: Become an owner and share in our success through our stock option program
Unlimited Paid Time Off: Take the time you need to recharge and maintain a healthy work-life balance
Spending Accounts: Manage your healthcare and dependent care expenses with tax-advantaged spending accounts
Wellness Days: Prioritize your mental and physical health with dedicated wellness days throughout the year
Growth Opportunities: We invest in your future with abundant opportunities for professional development and advancement
Mentorship Program: Benefit from guidance and support from experienced leaders in your field
Flexible Ways of Working: Enjoy the freedom to work in a way that suits your life and boosts your productivity

The Application Process:

We believe applying for a job should be straightforward and transparent. Here’s what to expect:

Submit Your Application: You’ll receive a confirmation email right away.
Intro sessions: Learn more about our culture, get alignment on your compensation expectation prior to committing to next steps
Take-home assessment
Meet the Engineering Team: Dive into technical discussions and learn how you can make an impact at League.
Final Steps: Meet our cross-functional team and the hiring managers and share experiences on collaboration
Offer and onboarding!

We value your time and effort—our team is committed to providing updates throughout the process.

Security-related Responsibilities

Compliance with Information Security Policies
Compliance with League’s secure coding practice
Responsibility and accountability for executing League's policies and procedures
Notification of HR, Legal, Compliance & Security of any incidents, breaches or policy violations

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

$106,000—$117,800 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 recruitinginfo@league.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:

Learn about our platform, leadership team and partners
Highmark Health, Google Cloud, League: new digital front door to seamless care
Former Providence President and Workday EVP of Corporate Strategy join League Board of Directors
League raises $95 million USD in Series C to build world’s leading healthcare CX platform
Forbes x League: The Platformization Of Healthcare Is Here
Fast Company x League: If we want better innovations in healthtech, we need more competition

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.

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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.

Privacy Policy

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