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 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: 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. Qualifications 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: 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 Off. Spending Accounts: tax‑advantaged accounts for healthcare and dependent care expenses. Wellness Days: dedicated wellness days throughout the year. Growth Opportunities: professional development and advancement. Mentorship Program: guidance and support from experienced leaders. 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. Compensation Range (Canada Only) $94,900 - $115,900 CAD 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 recruitinginfo@league.com . Application Process 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. 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. #J-18808-Ljbffr