Managing Director, Enterprise Capability & Learning Transformation

Managing Director, Enterprise Capability & Learning Transformation

This role will redefine how the enterprise builds capability for the future of work—architecting a modern, AI-enabled ecosystem that continuously develops the skills needed to lead through change, disruption, and rapid technology evolution.

Reporting to a member of the HR Leadership Team (HRLT), this role operates at the highest levels of the organization and directly influences enterprise strategy, workforce transformation, and long-term business performance. This leader will be responsible for reimagining how learning, skills, and capability-building are integrated into the fabric of the organization—ensuring employees are equipped to succeed in an increasingly AI-powered and dynamic environment.

Role Scope & Organizational Impact

• Lead an enterprise learning and capability organization of ~40 professionals, including 2 Directors, 5 Senior Managers, and a team of individual contributors
• Operate as a key member of the extended HR leadership team, partnering directly with HRLT and enterprise executives
• Own the strategy, design, and evolution of the enterprise learning and capability ecosystem
• Act as a transformational leader responsible for shifting the organization from traditional learning models to a modern, skills-based, continuously evolving capability engine
• Drive alignment across HR, Strategy, Technology, and Business leaders to embed capability-building into enterprise transformation and business outcomes

Key Responsibilities

Enterprise Capability & AI Strategy

• Define and execute a multi-year enterprise capability strategy aligned to business transformation priorities across healthcare, PBM, and specialty businesses
• Lead the design and activation of an AI-first learning and capability strategy, including future-focused skill frameworks and capability models
• Establish clear expectations for AI-enabled work across all employee segments—from frontline to executive leadership
• Partner with HRLT, enterprise strategy, technology, and business leaders to align capability investments to growth, productivity, and transformation outcomes
• Translate external market trends and emerging technologies into forward-looking workforce strategies that anticipate how work will evolve

Learning & Capability Ecosystem Modernization

• Transform the enterprise learning function into a modern, skills-powered capability ecosystem that meets employees where they are and supports continuous development
• Architect and scale a next-generation learning ecosystem that integrates platforms, vendor partnerships, content, and talent systems
• Deliver personalized, role-based learning journeys, corporate academy models (e.g., AI, leadership, functional), and in-the-flow-of-work development experiences
• Evaluate and optimize learning platforms and vendor strategies to improve usability, adoption, and impact
• Establish governance, operating models, and product ownership structures for enterprise learning and capability development
• Integrate learning with talent strategy, workforce planning, and skills architecture to enable mobility, progression, and succession planning
• Leverage AI to personalize learning, accelerate content creation, and enhance the learner experience
• Drive a shift from event-based training to continuous, embedded capability development that directly supports business priorities

Enterprise Enablement, Adoption & Transformation

• Champion enterprise-wide adoption of learning and capability programs, improving engagement and clarity on “what good looks like” for employees at all levels
• Lead large-scale reskilling and upskilling initiatives to support workforce transformation and evolving business needs
• Build frameworks to clearly define skills, competencies, and career pathways—linking capability development to performance, growth, and advancement
• Partner closely with business stakeholders to surface capability needs and ensure alignment to transformation priorities
• Drive a “builder” mindset—creating solutions that are scalable, adaptive, and able to evolve alongside rapid advancements in AI and technology

Qualifications

Minimum Qualifications

• Bachelor’s degree required/ MBA or Master’s degree preferred
• 15+ years of progressive leadership experience in learning & development, talent strategy, workforce transformation, or related functions
• Experience leading AI/digital transformation initiatives and applying emerging technologies to workforce capability and learning strategies
• Proven track record leading