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Software Delivery Program Manager

League

League

Operations
Toronto, ON, Canada
CAD 117,300-143,300 / year + Equity
Posted on Jun 27, 2025
About League

Founded in 2014, and with a total funding currently at $220 million; League is a platform technology company powering next-generation healthcare consumer experiences. Payers, providers, consumer health partners and employers build on League’s platform to deliver high-engagement, personalized healthcare experiences consumers love. Millions of people use solutions powered by League to access, navigate and pay for care.

As Software Delivery Program Manager, you are responsible for managing multiple concurrent software delivery projects for customers from discovery through to successful customer onboarding and solution adoption. You have full accountability for project success including schedule, quality, cost, and customer satisfaction.

You will develop end-to-end delivery plans and lead a cross-functional team to execute those plans. You will manage both technical and non-technical discussions, and take a proactive approach to anticipating and mitigating risks with clear action plans. You will communicate both internally and externally at all levels to manage trade-offs and drive effective decision-making with a view to maximizing long-term customer value realization.

You will act as a primary liaison between our cross-functional team and our customer, and build trusted relationships at all levels.

In this role, you will:

    • Lead Project Execution: Take ownership of one or more project plans to deliver customer solutions, including technical deliverables and dependencies, status reports, risk logs, and issue management. You'll manage program calendars and meeting schedules to ensure timely execution.
    • Drive Client Success: Act as the primary point of contact for clients and decision-makers, proactively managing expectations and leading discussions on implementation and project activities. Your focus will be on delivering a successful onboarding experience that fosters long-term customer value.
    • Cross-Functional Collaboration & Guidance: Collaborate closely with internal teams (Marketing, Communications, Product, Engineering, and Operations) to ensure alignment, communicate project status, and escalate issues. You'll motivate and guide these teams to deliver on time and to customer requirements.
      • Leadership Contribution: You'll lead project-specific initiatives and serve as a key point of contact for project-related decisions and direction.
      • Influence & Persuasion: You'll influence stakeholders to ensure project alignment and drive consensus on critical decisions, utilizing your communication skills to gain buy-in.
      • Team Building Support: You'll support a collaborative and positive team environment within your projects, contributing to team morale and fostering effective working relationships.
    • Problem-Solve & Mitigate: Employ strong problem-solving skills to navigate challenges and uncertainty during implementation and product development. You'll identify dependencies, coordinate with teams to ensure their attainment, and mitigate risks to maintain delivery schedules.
    • Manage Scope & Quality: Support change control processes and governance meetings to ensure project scope and timeline integrity. You'll also act as a liaison for testing initiatives, ensuring a smooth testing lifecycle with clients.
    • Continuous Improvement: Facilitate project retrospectives and technical RCAs to lead continuous improvement in software delivery practices.

About You:

  • 10+ 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
  • Experience with customer relationship management required

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
  • Flexible Ways of Working: Enjoy the freedom to work in a way that suits your life and boosts your productivity

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

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
$117,300$143,300 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 recruitinginfo@league.com.

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:

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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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