Managing Director, Enterprise Capability & Learning Transformation

The Cigna Group•Bloomfield, CT

3d•$196,600 - $327,600•Remote

About The Position

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.

Requirements

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 large-scale, enterprise-wide transformation initiatives
Demonstrated experience building, scaling, or reinventing enterprise learning, capability, or talent ecosystems
Strong data and analytics orientation, with the ability to measure adoption, effectiveness, and ROI of capability-building initiatives
Strong executive presence with the ability to influence and partner with senior leaders, including C-suite stakeholders
Experience operating in regulated industries; healthcare experience preferred
Background in consulting, strategy, or transformation-led environments with a focus on enterprise change
Deep experience in skills-based workforce transformation, including development of skills architecture, competency frameworks, and career pathways
Proven success designing and implementing modern, technology-enabled learning ecosystems (e.g., corporate academies, in-the-flow-of-work learning, personalized learning journeys)
Experience managing complex vendor ecosystems and learning technology platforms (e.g., LMS/LXP, content providers, AI-enabled tools)
Enterprise strategy development and operating model design at scale
Strong AI and digital fluency, with the ability to translate emerging technologies into practical workforce and capability outcomes
Deep expertise in skills-based workforce transformation, capability building, and enterprise change leadership
Proven ability to design and scale modern, technology-enabled learning ecosystems
Vendor strategy and ecosystem management experience
Exceptional executive stakeholder management, with experience influencing C-suite leaders and shaping enterprise priorities
Data-driven mindset with strong focus on adoption, outcomes, and ROI
Transformational builder with a track record of creating and scaling modern capability or learning functions
Strategic, forward-thinking leader comfortable challenging the status quo and reimagining how organizations develop talent
Strong AI and digital acumen, with the ability to translate disruption into actionable workforce capability strategies
Enterprise influencer with executive presence and credibility at the C-suite level
Operates effectively in ambiguity and thrives in environments undergoing significant change
Combines strategic vision with execution discipline to drive measurable business impact

Responsibilities

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
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
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