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.

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