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.
League is seeking a Director / AVP, Delivery Enablement & Excellence to build and lead a new function responsible for delivery infrastructure, governance, and organizational transformation across the entire Delivery organization.
This is a senior leadership and transformation role. You will own the systems, standards, and capabilities that enable League’s delivery teams to operate with consistency, predictability, and quality at scale. Your mandate spans four interconnected pillars: Delivery Enablement (methodology, training, knowledge management, and tooling), Financial Performance (delivery P&L, margin analysis, and resource supply/demand modeling), and Excellence & Transformation (talent development, competency frameworks, Centers of Excellence, and strategic transformation programs).
You will take League’s delivery organization from reliance on individual heroics to a systematic, scalable, and repeatable operating model. This requires building a dedicated team from scratch, defining the standard delivery playbook, and driving organization-wide adoption through deliberate change management. The role has a direct and measurable impact on League’s margin improvement trajectory from 15% to 25%.
Reporting to the Chief Delivery Officer with a dotted line to the CTO for technical standards, you will sit on the Executive Delivery Council alongside the VP Program Management, SVP Solutions Engineering & Delivery, VP, Client Solutions and SVP Member & Employer Services. You will also lead the Delivery Operations Review and Talent & Development Council governance forums.
1. Delivery Methodology & Standards
Define, implement, and continuously refine the Standard Delivery Playbook covering the end-to-end delivery lifecycle from discovery through deployment and post-implementation optimization.
Establish scalable intake, planning, estimation, and release governance processes.
Drive consistency in Agile practices, sprint hygiene, dependency management, and release readiness across all delivery teams.
Develop playbooks, templates, checklists, and documentation to enable repeatable execution across squads, client programs, and external partners.
2. Training, Onboarding & Certification
Own onboarding and continuous training programs for all delivery staff including engineers, project managers, product managers, designers, and QA testers.
Develop and deliver role-based training on product and business context, scoping and discovery, technical standards, project management methodology, and client communications.
Build a tiered certification program (Associate, Professional, Expert) to formalize competency development across the delivery organization.
Reduce time-to-productivity for new hires (target: 30 days to 60% productivity).
Extend enablement programs to SI partners and Developer Program customers to ensure consistent operational standards.
3. Tooling, Knowledge Management & AI
Own the standard Jira process: define the desired workflow, then configure the tool to match delivery needs. Drive 100% adoption.
Build and maintain a centralized platform knowledge repository organized by audience (engineer, PM, customer developer) with tiered content.
Own and maintain shared code libraries and design component libraries to promote reusability and consistency.
Drive adoption of AI tooling and workflows within the delivery organization; develop an AI-native delivery framework.
4. R&D Partnership & Release Enablement
Establish and manage a formal operating agreement with R&D covering platform documentation, dedicated SME access, and release readiness commitments.
Translate R&D documentation into delivery-focused training materials and maintain feedback loops on common implementation challenges.
Implement a Release Enablement gate in the R&D release process ensuring training materials, documentation, team briefings, and customer communications are ready before GA.
5. Delivery P&L & Margin Optimization
Own delivery P&L management and forecasting in partnership with Finance.
Conduct project margin analysis and drive optimization initiatives toward the 25% target.
Quantify expected impact of enablement initiatives on utilization efficiency, rework reduction, and delivery velocity.
Support commercial model development, pricing discipline, and cost management.
6. Talent Development & Organization Design
Develop delivery competency frameworks and career pathing for all delivery roles.
Partner with VPs and SVPs on hiring plans, performance management, and team capability building.
Lead the Talent & Development Council governance forum with all Delivery VPs.
Drive employee engagement and retention within the delivery organization.
7. Transformation Program Management
Own the strategic transformation program to move the delivery organization from current state to target operating model.
Establish and evolve Centers of Excellence for specialized domains.
Manage Board reporting and strategic communications related to delivery transformation progress.
Design and execute a change management strategy (ADKAR framework) to drive adoption of new processes and standards.
Build a coalition of champions across Engineering, PM, Design, and QA to evangelize new approaches.
Implement a graduated adoption approach—voluntary to strongly encouraged to mandatory—with documented exceptions.
8. Growth & Commercial Operations (Shared)
New customer implementation methodology development.
Onboarding playbooks and acceleration frameworks.
Commercial delivery strategy including packaging/pricing models and service catalog development.
Partner ecosystem development for delivery models.
10+ years in delivery operations, program management, or engineering operations within a SaaS or digital platform environment, with progressive leadership responsibility.
Proven track record building delivery organizations “from chaos to order”—demonstrated success standing up new functions, defining standard operating models, and driving large-scale process transformation and adoption.
P&L management experience: ownership of or significant contribution to delivery financial performance, margin analysis, and resource planning.
Proven experience working closely with Software Engineering teams and credibly engaging with technical audiences on architecture, SDLC, and tooling decisions.
Experience operating in complex, multi-client or multi-workstream environments with both onshore and offshore delivery teams.
Enablement and training experience: ability to build and deliver scalable training materials, onboarding programs, and certification curricula.
Organizational change management expertise with demonstrated success driving adoption across cross-functional teams at scale.
Experience building and managing high-performing teams as well as coordinating matrixed resources across multiple functions.
Prior experience in digital health, health tech, or highly regulated environments is a strong asset.
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/ team
Notification of HR, Legal, Compliance & Security of any incidents, breaches or policy violations
Compliance with Information Security Policies
US APPLICANTS ONLY: The US-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 US 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 USA applicants only
$212,200—$259,400 USD
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.
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:
Highmark Health, Google Cloud, League: new digital front door to seamless care
Former Providence President and Workday EVP of Corporate Strategy join League Board of Directors
League raises $95 million USD in Series C to build world’s leading healthcare CX platform
Fast Company x League: If we want better innovations in healthtech, we need more competition
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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Visit website$212,200 – $259,400
Base + Bonus · Other Equity
