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
We are seeking a skilled Software Engineer to join our Release Engineering team, focusing on CI/CD infrastructure, release automation, and developer tooling. This role combines hands-on development with operational excellence to support our engineering organization's delivery capabilities.
In this role, you will:
Release Management & Automation:
Manage and execute releases across multiple platforms (Web, Android, iOS, CLIs)
Develop and maintain release automation tools and bots
Handle release patch/hotfix requests and coordinate release schedules
Troubleshoot and resolve release automation issues, including rollback procedures
Use AI to help scale solutions and streamline existing processes
Infrastructure & CI/CD:
Work with the team to implement CI/CD infrastructure improvements, including migration to self-hosted runners
Identify methods to optimize build performance and reduce pipeline execution times
Manage CircleCI-hosted runners and Kubernetes infrastructure
Maintain Docker execution environments for build and release pipelines
Identify and act on opportunities to optimize resource utilization and developer productivity.
Platform-Specific Development:
Work on app security improvements and certificate management
Develop CLI tools and manage external/internal release pipelines
Handle cross-platform builds
Developer Experience & Tooling:
Research and implement AI-assisted development tools for SDK migrations
Collaborate with security teams on compliance and best practices
Desired Outcomes
Gain a deep understanding of the release processes followed across different deployment models.
Develop scalable solutions that optimize the time required to manage major, minor, and patch releases for customers.
About You:
Knowledge of cloud platforms (GCP preferred)
Background in mobile app development and distribution
Experience with CLI tool development and distribution
Strong experience with CI/CD systems
Proficiency in containerization (Docker, Kubernetes)
Experience with release management and automation
Knowledge of mobile development and security practices
Familiarity with monitoring and observability tools
Attributes / Characteristics
Problem-solving skills for infrastructure and build optimization
Ability to work independently and manage multiple concurrent projects
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.
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 [email protected].
- 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.
- 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.
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.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.
