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. Your responsibilities include:

In this role, you are expected to:

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 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

Please note: We’re always excited to connect with exceptional talent. This posting is part of our proactive talent community efforts. While there may not be an immediate opening, we review applications on an ongoing basis and reach out as opportunities arise.

CANADA APPLICANTS ONLY: The Canada-specific compensation range below for this full-time position is exclusive of bonus, equity and benefits. This range reflects the minimum and maximum target for base salaries for the position across all Canadian locations. The salary range is intentional to account for the performance and career progressions a Leaguer will experience in the role throughout their time at League. Where in the band you may land is determined by job-related skills/experience. Your recruiter can share more about the specific salary range specific to your skills and experience during the hiring process.

Compensation range for Canada applicants only

$94,900—$115,900 CAD

Our employees come from different backgrounds, and we celebrate those differences. We are looking for the best candidates for our open roles, but do not expect applicants to meet every qualification in order to be considered. If you are excited about what you could accomplish at League and believe you can add value to our team, we would love to hear from you.

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 [email protected].

Our Application Process:

Applying to a role you love can be exhausting, and understanding the next steps can feel vague and uncertain. You have done the hard part of submitting your application; let's do ours by sharing potential next steps

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.

Here are some additional resources to learn more about League:

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 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.

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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.

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Technical Delivery Project Manager (Talent Pool Building)

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