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 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

Preferred Qualifications

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)

Capabilities

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

Leadership Profile

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

If you will be working at home occasionally or permanently, the internet connection must be obtained through a cable broadband or fiber optic internet service provider with speeds of at least 10Mbps download/5Mbps upload.

For this position, we anticipate offering an annual salary of 196,600 - 327,600 USD / yearly, depending on relevant factors, including experience and geographic location.

This role is also anticipated to be eligible to participate in an annual bonus and long term incentive plan.

At The Cigna Group, you’ll enjoy a comprehensive range of benefits, with a focus on supporting your whole health. Starting on day one of your employment, you’ll be offered several health-related benefits including medical, vision, dental, and well-being and behavioral health programs. We also offer 401(k), company paid life insurance, tuition reimbursement, a minimum of 18 days of paid time off per year, paid holidays, and leaves of absence. For more details on our employee benefits programs, click here.

About The Cigna Group

Doing something meaningful starts with a simple decision, a commitment to changing lives. At The Cigna Group, we’re dedicated to improving the health and vitality of those we serve. Through our divisions Cigna Healthcare and Evernorth Health Services, we are committed to enhancing the lives of our clients, customers and patients. Join us in driving growth and improving lives.

If you need a reasonable accommodation to complete the online application process, please email seeyourself@thecignagroup.com for assistance. Please note that this email inbox is dedicated to accommodation requests only and cannot provide application updates or accept resumes.

The Cigna Group has a tobacco-free policy and reserves the right not to hire tobacco/nicotine users in states where that is legally permissible. Candidates in such states who use tobacco/nicotine will not be considered for employment unless they enter a qualifying smoking cessation program prior to the start of their employment. These states include: Alabama, Alaska, Arizona, Arkansas, Delaware, Florida, Georgia, Hawaii, Idaho, Iowa, Kansas, Maryland, Massachusetts, Michigan, Nebraska, Ohio, Pennsylvania, Texas, Utah, Vermont, and Washington State.

Qualified applicants with criminal histories will be considered for employment in a manner consistent with all federal, state and local ordinances.