Delivery Manager

About League

 

League is one of the fastest-growing technology companies in Canada and the leading healthcare experience platform. Getting healthcare is often the easy part — finishing it is where things fall apart: people book the appointment and skip the follow-up, fill the prescription and stop taking it, get the referral and never make the call. That gap costs health plans and health systems money, and it costs people their health. League closes that gap — identifying what each person needs to do next, clearing what’s in their way, and getting it done, for the 70 million+ people whose care already runs through our platform. Health plans and health systems trust us to do this at scale. Organizations like Manulife, SCAN, Geisinger, and Medibank on the payer side, and Baptist and Shoppers Drug Mart on the provider side. 

Position Summary:

As a Delivery Project Manager , you are responsible for the successful delivery of SaaS projects for League customers. You manage defined project scope and timeline, coordinate internal and external stakeholders, and ensure customers are onboarded effectively.

You create and manage detailed project plans, facilitate execution of deliverables, communicate progress, risks, and issues, and act as a liaison between customers and League’s cross-functional teams. You manage both technical and non-technical discussions, helping translate risks into actionable tasks and guiding internal teams toward timely completion. While you operate with growing independence, you receive direction and support for complex or escalated matters.

This contract role is foundational within our Delivery team and develops the executional, communication, and customer leadership skills required to progress into more senior delivery roles. 

What You'll Do:

Project Leadership & Execution

• Manage one or more implementation projects against scope, schedule, quality expectations.
• Build and maintain project plans, status reports, and risk/issue logs.
• Coordinate project schedules, customer meetings, and internal working sessions.
• Track deliverables and ensure task owners remain accountable to timelines.

Customer Engagement & Communication

• Serve as a reliable point of contact for customers during onboarding.
• Lead customer discussions related to project progress, upcoming tasks, or risks.
• Set and reset expectations with customers and internal stakeholders as needed.
• Proactively identify barriers to success and escalate appropriately.

Cross-Functional Collaboration

• Partner with cross-functional teams to ensure completion of project milestones.
• Coordinate discovery discussions, requirement refinement, and testing preparation.
• Support change-control discussions and contribute to governance processes.

Risk, Issue & Dependency Management

• Identify risks early and work with internal teams to mitigate impacts.
• Support dependency tracking and cross-functional alignment.

Testing & Delivery Quality

• Support testing activities throughout the implementation lifecycle.
• Act as the liaison between customers and League’s testing teams.
• Ensure documentation and deliverables remain organized and up to date.
• Support defect tracking and triage throughout testing cycles, ensuring clear documentation, prioritization, and timely reporting of defects to the customer.

Process & Continuous Improvement

• Apply project management best practices and contribute to improving processes and tools.
• Gather customer feedback through a standard retrospective process and support continuous improvement of the delivery process.
• Foster referenceable clients through a high-quality onboarding experience.

About you:

• 2-4 years of implementation, project management, or related delivery experience.
• Experience working directly with customers in technology, healthcare, or consumer applications.
• Bachelor’s degree or equivalent work experience.
• Familiarity with SaaS delivery and technical onboarding is an asset.

Security-Related Responsibilities

• Compliance with all Information Security Policies.
• Responsibility for secure handling of customer data and project documentation.
• Required to report any incidents or violations promptly.

 

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

 

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

$75,000—$90,000 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 View email address on job-boards.greenhouse.io .

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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