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League

Technical Delivery Project Manager

Hybrid

Toronto, Canada

Full Time

26-01-2026

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Skills

Jira Data Engineering Test Analytics Data Science Artificial Intelligence

Job Specifications

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 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 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.

In This Role, You Are Expected To

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:

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.

Jira & Tooling Ownership

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.

Risk & Issue Management

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.

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 Informa

About the Company

Founded in 2014, League is a platform technology company powering next-generation healthcare consumer experiences. Payers, providers, consumer health partners and employers build on League’s platform to deliver high-engagement, personalized healthcare experiences consumers love. Millions of people use solutions powered by League to access, navigate and pay for care. Know more