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 whats 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.

The Role

As Principal, Delivery, you are accountable for meeting customer deliverables as per contractual agreements (scope and time), and internal budget. The ideal candidate will drive and guide disciplined execution through the use of consistent methodologies, processes, and strong communication skills. You will be a passionate advocate for the League product and ensure the platform is implemented on time and with high quality to meet our clients business needs.

In this role, you are expected to:

Manage, lead and oversee one or more client implementations and internal company and/or team initiatives simultaneously
Implement the project governance structure, including delivery structure, change control and processes to support risk and issue escalation, decision making and program status
Lead the organization and deployment of League resources for implementation, the production of deliverables, and the oversight of timelines to ensure a seamless delivery of League products to clients
Accountable for build and maintenance of end to end integrated program plans, resource assignments, budgets and performance against targeted implementation milestones for the implementation and teams
Serve as escalation point for risks, issues, and decisions one or more implementations simultaneously
Maintain a deep understanding of Leagues product and platform to inform key business requirements and decisions during implementations
Lead internal teams and the client on a successful change management plan by creating deliverables based on client pain points and objectives
Collaborate on communication plans and drive accountability for obtaining final approvals on client deliverables
Develop and manage a high performing team by providing direction and guidance both on the job and as a career coach to Implementation team members
Coach and develop staff to have a deep understanding of implementation delivery methodology and the Leagues product and platform
Lead key internal initiatives to drive efficiencies and best practices for implementation processes, workflows, and tools
Accountable for implementation client satisfaction scores and referenceable implementation clients
Partner with Customer Strategy and Member Services teams to lead a smooth client transition from implementation to ongoing operations and account management
Collaborate with the client lead from Customer Strategy to drive a smooth client transition from the sales cycle to implementation for the client and League teams

About You:

Minimum 10 years in healthcare management, delivery and/or consulting experience
10+ years of client management and/or program management required
Prior engagement management and/or team management experience serving as the primary interface with senior client executive sponsors
Proven track record of strong client management and customer service skills
Strong leadership skills and a drive to make a large impact on the company and its clients
Excellent written and oral presentation skills, with the ability to engage, inspire, build credibility and engender trust across all levels of an organization.
Strong business and technical acumen, and executive presence, combined with deep analytical and organizational skills
Results-oriented individual with a history of setting and attaining goals and meeting aggressive timelines
Confident, capable, enthusiastic self-starter with minimal need for direction
Experience at a SaaS, health-tech company, and/or start-up company highly preferred
Experience with project management software and tools
Bachelors degree or equivalent years of experience

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

Ensure access management is performed in compliance with the employee's role and responsibilities
Responsibility and accountability for executing League's policies and procedures within the department and team
Notification of HR, Legal, Compliance & Security of any incidents, breaches or policy violations
Compliance with Information Security Policies

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

$140,900—$176,100 CAD

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

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:

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 roles 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, youll 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.

Privacy Policy

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Principal, Delivery

League Inc.

Job Description