LEAD DIRECTOR, ENTERPRISE TRANSFORMATION EXECUTION - CT - Hartford | CVS Health Job

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.

Position Summary

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.

Required Qualifications

• 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.

Preferred Qualifications

• 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.

We welcome candidates from consulting, technology, operations, customer experience, financial services, retail, and other large-scale transformation environments. Strong business curiosity, executive presence, and a willingness to immerse quickly in the healthcare ecosystem matter more than industry tenure.
Education

• Bachelor’s degree or equivalent experience.

Pay Range

The typical pay range for this role is:

$100,000.00 - $231,540.00

This pay range represents the base hourly rate or base annual full-time salary for all positions in the job grade within which this position falls.  The actual base salary offer will depend on a variety of factors including experience, education, geography and other relevant factors.  This position is eligible for a CVS Health bonus, commission or short-term incentive program in addition to the base pay range listed above.  This position also includes an award target in the company’s equity award program. 
 

Our people fuel our future. Our teams reflect the customers, patients, members and communities we serve and we are committed to fostering a workplace where every colleague feels valued and that they belong.

Great benefits for great people

We take pride in offering a comprehensive and competitive mix of pay and benefits that reflects our commitment to our colleagues and their families.

This full‑time position is eligible for a comprehensive benefits package designed to support the physical, emotional, and financial well‑being of colleagues and their families. The benefits for this position include medical, dental, and vision coverage, paid time off, retirement savings options, wellness programs, and other resources, based on eligibility.

Additional details about available benefits are provided during the application process and on Benefits Moments.

We anticipate the application window for this opening will close on: 10/03/2026

Qualified applicants with arrest or conviction records will be considered for employment in accordance with all federal, state and local laws.