Director / Assistant Vice President of Delivery Enablement & Excellence, League
$212.2-259.4k
Expert level
Remote from US
Consumer experience platform for healthcare
Be an early applicant
Consumer experience platform for healthcare
501-1000 employees
HealthcareB2BPersonal healthSaaSData Analysis
Be an early applicant
$212.2-259.4k
Expert level
Remote from US
501-1000 employees
HealthcareB2BPersonal healthSaaSData Analysis
Company mission
To power next-generation healthcare experiences with a platform built to enable CX transformation.
Role
Who you are
- 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
What the job involves
- 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
- PILLAR 1: DELIVERY ENABLEMENT
- 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
- 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
- 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
- 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
- PILLAR 2: FINANCIAL PERFORMANCE
- 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
- PILLAR 3: EXCELLENCE & TRANSFORMATION
- 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
- 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
- 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
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
Our take
Health benefits are a top requirement for anyone seeking a new job in the US today, but classic one-size-fits-all plans are no longer regarded fit for service. League's platform - for payers, providers, consumer health businesses, and employees - connects all benefits in one HIPAA-compliant place, to enable all bodies involved with health benefits to provide better customer healthcare experiences.
League is already one of the bigger players in the employee wellness space, having capitalised on the recently accepted correlation between employee health and productivity to secure huge clients like Uber, Shopify and Unilever. The company has seen significant investment, which will support the scaling of its platform-as-a-service offering. With more than 63 million contracted users, it is securing its position as the leading digital infrastructure for an integrated health ecosystem.
Freddie
Company Specialist at Welcome to the Jungle
Insights
Top investors
-4% employee growth in 12 months
Company
Funding (last 2 of 4 rounds)
Feb 2022
$95m
SERIES C
Jul 2018
$47.1m
SERIES B
Total funding: $171.1m
Company benefits
- Flexible medical and dental plans
- 401(k) and RRSP matching programs
- Health, lifestyle, learning and family spending accounts
- Employee stock option program (ESOP)
- Generous leaves (including parental and sabbatical)
- Flexible time off
Company HQ
Entertainment District, Toronto, ON
Leadership
Michael Serbinis
(Founder & CEO)Founder of DocSpace and Kobo. Experience as CEO for Three Angels Capital and Board Director for Vector Insitute, among other prominent business leadership roles.
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