Lead Director, Enterprise Transformation Execution

CVS Health•Hartford, CT

About The Position

We’re building a world of health around every individual — shaping a more connected, convenient and compassionate health experience. At CVS Health®, you’ll be surrounded by passionate colleagues who care deeply, innovate with purpose, hold ourselves accountable and prioritize safety and quality in everything we do. Join us and be part of something bigger – helping to simplify health care one person, one family and one community at a time. The Lead Director, Enterprise Transformation Execution is one of three leadership seats in the Service Operations Strategic Advisor Office, reporting to the Chief of Staff. The office is deliberately built around three different jobs running at three different clock speeds: run the business — management processes, the Service Operations operating cadence and value realization governance; change the business — this seat; and carry the culture — colleague experience, communications and change management. This seat owns the change agenda: day-to-day delivery of enterprise transformation workplans and milestones, the executive governance and decision forums that keep them moving, and execution of the Service Model north star. The work is finite, sequenced, and unforgiving of part-time attention — it is measured on whether a defined set of transformation commitments land on time and are adopted. This is a senior individual contributor role working in coordination with the Service Operations Transformation PMO and the office’s run-the-business seat. Leverage comes from integrated planning, sharp executive decision support, and influence across business, operations, technology, digital, product, clinical, finance, compliance and external partners — not from a delivery team of its own.

Requirements

10+ years in strategy, operations, transformation, program management, consulting, or business performance
Proven success leading large-scale, cross-functional initiatives in highly matrixed organizations
Track record of carrying a defined program end to end — plan, governance, milestones, and adoption — not only supporting one
Demonstrated ability to influence without direct authority and to deliver as a senior individual contributor
Exceptional executive communication and presentation skills, including experience presenting to senior executives
Strong analytical, problem-solving, and organizational capabilities
Bachelor’s degree or equivalent experience

Nice To Haves

Enterprise PMO, business transformation, strategic execution, or large-scale program delivery leadership
Chief of staff, strategy office, or transformation office experience supporting an executive leadership team
Service or operating model design and target-state roadmap execution
Scaling automation and AI capabilities across multiple functions — converting proven pilots into reusable, governed playbooks and standardized deployment patterns
Working knowledge of digital transformation, AI-enabled operations, customer experience, service delivery models, or operating model design
Health care, insurance, or other regulated service operations environments
Strong business curiosity, executive presence, and a willingness to immerse quickly in the healthcare ecosystem matter more than industry tenure

Responsibilities

Day-to-day delivery of enterprise transformation workplans and milestones
Executive governance and decision forums that keep transformation work moving
Execution of the Service Model north star
Ensuring a defined set of transformation commitments land on time and are adopted