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.

Software Delivery Project Manager

As a Software Delivery Project Manager, you are responsible for managing multiple concurrent projects to deliver solutions to customers. You will work closely with a Software Delivery Program Manager and a cross‑functional team to create and execute end‑to‑end project plans, balancing schedule, quality, cost, and customer satisfaction. You will proactively and strategically manage software delivery, from discovery through to successful customer adoption, managing dependencies, leading technical discussions, and driving action plans to resolve issues and mitigate risks.

You will support clear communication on project status to all stakeholders, supported by transparent KPIs, and act as a primary liaison between the cross‑functional team and our customer, building trusted relationships at all levels.

Responsibilities - Support Project Execution: Take ownership of one or more project plans,



including status reports, risk logs, and issue management. Manage program calendars and meeting schedules to ensure timely execution.

- Cross‑Functional Collaboration & Guidance: Collaborate closely with internal teams (Marketing, Communications, Product, Engineering, and Operations) to ensure alignment, communicate project status, and address issues. Motivate and guide these teams to deliver on time and to customer requirements.
- Problem‑Solve & Mitigate: Employ strong problem‑solving skills to navigate challenges and uncertainty during implementation and product development. Identify dependencies, coordinate with teams, and mitigate risks to maintain delivery schedules.
- Manage Scope & Quality: Support change control processes and governance meetings to ensure project scope and timeline integrity. Act as a liaison for testing initiatives, ensuring a smooth testing lifecycle with clients.
- Continuous Improvement: Manage deliverable and document control processes. Capture ongoing customer feedback and support internal initiatives to develop and improve documentation and processes, contributing to League’s evolving delivery model.
- Best Practices:



Apply project management best practices, tools, and processes per internal standards, partnering with Delivery Leads to overcome barriers to project success. 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 What You’ll Bring - 5+ years experience in a high‑performance software delivery capacity - 5+ years of project management experience preferred - Bachelor’s degree or equivalent - Experience in the healthcare, consumer applications or technology required 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 and enjoy flexible remote days each quarter. 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].

📌 Delivery Manager (Toronto)
🏢 Portage Ventures GP
📍 Toronto