Technical Delivery Project Manager; Talent Pool Building

About League

Founded in 2014, League is the leading healthcare consumer experience (CX) platform powered by artificial intelligence (AI). It services over 63 million people worldwide and partners with payers, providers, and consumer health brands to deliver personalized healthcare solutions that improve health outcomes.

As a Technical Delivery Project Manager you will coordinate internal technical work streams required for customer delivery. You will serve as the day‑to‑day liaison between internal technical teams (Data Engineering, Data Science, Integrations, R&D) and the customer‑facing delivery team. Your focus will be on translating customer requirements into technical tasks, managing documentation, and ensuring timely completion of technical deliverables.

• 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 configuration and customization of AOs and other data products to meet customer use cases.
• Attend customer‑facing technical requirement meetings and document technical requirements.
• 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 work streams and escalate issues to the Delivery Lead or technical leads as needed.
• Support internal test cycles, data validation activities, and technical documentation requirements.
• Maintain technical requirement documentation, task tracking, and workstream‑level artifacts.
• Contribute feedback to improve technical delivery processes and tooling.

• Compliance with Information Security Policies.
• Adherence to League’s secure coding practice.
• Accountability for executing League’s policies and procedures.
• Notification to HR, Legal, Compliance & Security of any incidents, breaches, or policy violations.

• 3+ years in SaaS technical coordination, technical support, or data operations.
• Working knowledge of data platforms (Airflow, Big Query, 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.

• Use AI tools to enhance productivity, problem‑solving, and decision‑making.
• Apply judgment and accountability when using AI by reviewing outputs for accuracy, bias, and quality.
• Continuously learn and adapt as new AI tools and capabilities emerge.
• Identify opportunities to improve workflows by leveraging AI effectively.
• Operate with strong data responsibility and security awareness when working with sensitive or regulated information.

• Comprehensive health benefits (medical, dental, vision).
• Performance‑based bonus program.
• Employee stock option program.
• Unlimited paid time off.
• Spending accounts for healthcare and dependent care expenses.
• Wellness days.
• Growth opportunities and professional development.
• Mentorship program.

$94,900 - $115,900 CAD (excluding bonus, equity, and benefits). The specific base salary will be determined based on job‑related skills and experience.

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