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), 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.

Responsibilities

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: complete medical, dental, and vision coverage.
• Bonus Program: performance‑based bonus.
• Employee Stock Option Program: ownership and sharing in success.
• Unlimited Paid Time Off.
• Spending Accounts: tax‑advantaged healthcare and dependent care accounts.
• Wellness Days: dedicated days for mental and physical health.
• Growth Opportunities: professional development and advancement.
• Mentorship Program: guidance 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.

AI Fluency & Ways of Working

At League, we are an AI‑native organization. We expect all employees regardless of role or level to thoughtfully leverage AI to improve the quality, speed, and impact of their work.

What this means in practice

• Use AI tools as part of your daily workflow to enhance productivity, problem‑solving, and decision‑making (e.g., drafting, analysis, coding, research, or process automation).
• Apply judgment and accountability when using AI by reviewing outputs for accuracy, bias, and quality before use.
• Continuously learn and adapt as new AI tools and capabilities emerge, incorporating them into your ways of working.
• Identify opportunities to improve how work gets done from personal productivity to team‑level workflows by leveraging AI effectively.
• Operate with strong data responsibility and security awareness, especially when working with sensitive or regulated information.

How this scales by level

• Individual Contributors: use AI to improve personal productivity and quality of output.
• Senior ICs / Managers: integrate AI into team workflows and improve processes.
• Leaders: drive AI adoption at the organizational level and shape how work is done across teams.

What We Look For

• Demonstrated experience using AI tools in a practical, responsible way.
• Curiosity and openness to experimenting with new technologies.
• Ability to balance efficiency with quality and sound judgment.

Equal Employment Opportunity

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.

Our 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 and share the team‑specific interview process.
• 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.

Additional Resources

• Learn about our platform, leadership team and partners.
• Highmark Health, Google Cloud, League: new digital front door to seamless care.
• Former Providence President and Workday EVP of Corporate Strategy join League Board of Directors.
• League raises $95 million USD in Series C to build world's leading healthcare CX platform.
• Forbes x League: The Platformization Of Healthcare Is Here.
• Fast Company x League: If we want better innovations in healthtech, we need more competition.

Work Location

We have a mix of office‑centric roles based in our vibrant Toronto office, and remote‑eligible roles based anywhere in Canada or the 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.

Employment Scams

Recognize and avoid employment scams. Practice safe job searching. Scammers are getting craftier and leveraging fake job postings to get personal information. Know the warning signs and protect yourself from scammers. Learn more here.

Use of AI Notice

We are committed to ensuring fairness and transparency throughout our hiring process. League may use Artificial Intelligence (AI) tools to assist in the screening of applicants for this position. Please check out our stance on using AI in recruitment here.

Privacy Policy

Review our Privacy Policy for information on how League is protecting personal data.