Technical Delivery Project Manager (Talent Pool Building)

Technical Delivery Project Manager (Talent Pool Building)

Location: Toronto, ON

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 worldwide 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.

Role Overview

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 (Data Engineering, Data Science, Integrations, R&D) and the customer‑facing delivery team. You coordinate technical requirements, translate customer inputs into internal 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), a recurring data export of complex KPIs configured to meet a wide range of customer requirements.

Technical Workstream Coordination

• 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.

Manage Data Products

• 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.

Customer Engagement & Requirements Gathering

• 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.

Technical Delivery Support

• Support internal test cycles, data validation activities, and technical documentation requirements.
• Understand and articulate the impact of deviations from standard practices.

Process & Documentation

• 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.

Benefits

• Comprehensive Health Benefits: medical, dental, and vision coverage.
• Performance‑based Bonus Program.
• Employee Stock Option Program.
• Unlimited Paid Time Off.
• Spending Accounts for healthcare and dependent care expenses.
• Wellness Days to support mental and physical health.
• Growth Opportunities and professional development.
• Mentorship Program.

Security‑Related Responsibilities

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

Compensation

Compensation range for Canada applicants only:

$94,900 - $115,900 CAD

EEO Statement

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 View email address on ca.talent.com.

Job Status

Open for Application