About League
League is one of the fastest-growing technology companies in Canada and the leading healthcare experience platform. Getting healthcare is often the easy part — finishing it is where things fall apart: people book the appointment and skip the follow-up, fill the prescription and stop taking it, get the referral and never make the call. That gap costs health plans and health systems money, and it costs people their health. League closes that gap — identifying what each person needs to do next, clearing what's in their way, and getting it done, for the 70 million+ people whose care already runs through our platform. Health plans and health systems trust us to do this at scale. Organizations like Manulife, SCAN, Geisinger, and Medibank on the payer side, and Baptist and Shoppers Drug Mart on the provider side.
The Role
As a Technical Delivery Project Manager, you support the successful execution of internal technical workstreams required for customer delivery. You serve as the day-to-day liaison between internal technical teams (e.g., Data Engineering, Data Science, Integrations, R&D) and the customer-facing delivery team. You coordinate technical requirements, gather inputs from customers, help translate requirements into internal technical tasks, manage supporting documentation, and ensure technical deliverables are completed on time.
In this role, you work closely with the Delivery Lead and functional technical leads to ensure alignment, visibility, and smooth execution of technical dependencies. You apply strong working knowledge of tools like Jira and foundational technical literacy to understand and communicate risks, issues, and timelines. You operate with growing independence while receiving guidance for complex or ambiguous matters.
One specific area of responsibility is to manage League's customer-facing data product called Analytics Objects (AOs), which is a recurring data export of complex KPIs configured to meet a wide range of customer requirements. Your responsibilities include:
In this role, you are expected to:
- Coordinate technical tasks and dependencies across Data, Engineering, R&D, and other internal technical teams.
- Translate customer requirements into clear Jira tickets or internal work items.
- Maintain visibility into task progress, blockers, and timelines.
- Coordinate launch of Analytics Objects (AOs) and other data products to customers.
- Manage the configuration of AOs and other data products to suit customer use cases.
- Manage customization requests and recommend existing solutions to customers as needed. Coordinate with product managers on custom solutions.
- Attend customer-facing technical requirement meetings as a supporting point of contact.
- Document technical requirements and ensure internal technical teams understand expected outcomes.
- Communicate updates, risks, and next steps back to customer-facing stakeholders.
- Support maintaining Jira boards, grooming tasks, updating statuses, and ensuring accurate workflow progression for tasks related to customer delivery.
- Support reporting on technical delivery progress and timelines.
- Identify and flag risks or blockers related to technical workstreams.
- Escalate issues to the Delivery Lead or technical leads as needed.
- Support internal test cycles, data validation activities, and technical documentation requirements.
- Understand and articulate the impact of deviations from standard practices.
- Maintain technical requirement documentation, task tracking, and workstream-level artifacts.
- Contribute feedback to help improve technical delivery processes and tooling.
About You:
- 3+ years in SaaS technical coordination, technical support, or data operations.
- Working knowledge of data platforms (Airflow, BigQuery, Looker, or similar).
- Strong proficiency with Jira for workflow tracking and ticket management.
- Foundational understanding of SaaS architectures, APIs, data pipelines, or ETL.
- Experience collaborating with Data teams, R&D, or technical SMEs.
- Experience managing projects with complex technical dependencies.
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
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
Please note: We're always excited to connect with exceptional talent. This posting is part of our proactive talent community efforts. While there may not be an immediate opening, we review applications on an ongoing basis and reach out as opportunities arise.
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
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
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
[email protected].
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
Review our Privacy Policy for information on how League is protecting personal data.
