Technical Delivery Project Manager

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.

The Role

As a Technical Delivery Project Manager
, you support the successful execution of internal technical work streams 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:

• 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 work streams.
• 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.

• 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.

• Comprehensive
  
  Health Benefits:
  
  complete medical, dental, and vision coverage.
• Bonus Program: performance‑based bonus program.
• Employee Stock Option Program: share in our success through stock options.
• Unlimited Paid Time…