Director​/AVP, Delivery Enablement & Excellence

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.

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 r 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.

• 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.
• 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.
• 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.
• R&D Partnership & Release Enablement
• Establish and manage a formal operating…