Director IT Portfolio & Program Delivery - Regulatory & Strategic Programs

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 Director, IT Portfolio & Program Delivery, is a senior leadership role responsible for the strategic oversight, governance, and successful delivery of a large portfolio of technology initiatives. This individual will lead multiple complex programs and portfolios that span business units and technology organizations, ensuring alignment with enterprise objectives and business value realization.

The role requires a highly accomplished leader who can balance strategic portfolio management with hands-on program execution, while driving governance, operational excellence, and continuous improvement across project and delivery teams. The Director will partner closely with business leaders, technology stakeholders, and executive leadership to establish priorities, manage investments, mitigate risks, and ensure successful delivery of critical initiatives.

This leader will oversee portfolios representing significant financial investment and organizational impact, while fostering a culture of accountability, transparency, collaboration, and delivery excellence.

Required Qualifications

• 10+ years of experience in programming and portfolio management, including managing large-scale, complex technology and business transformation initiatives in large, matrixed organizations.
• 8+ years proven experience managing enterprise portfolios, including budgets exceeding $20M annually, with responsibility for strategic planning, prioritization, governance, and execution.
• 8+ years demonstrating deep expertise in portfolio governance, project management methodologies, risk management, budget management, and value realization practices.
• 6+ years’ experience establishing and continuously improving portfolio and program governance frameworks, including reporting structures, decision-making processes, KPI development, escalation protocols, and performance measurement.
• 6+ years’ experience with workforce planning, resource management, capacity planning, and dependency management skills.
• 5+ years of direct people leadership experience managing and developing teams of project, program, and portfolio management professionals.
• 5+ years’ experience developing metrics, procedures, objectives, and methods to assess portfolio health and organizational performance.
• 5+ years’ experience demonstrated strong executive communication, presentation, and stakeholder management skills with the ability to influence senior leaders and drive alignment across diverse stakeholder groups.
• 5+ years of expertise using project and portfolio management tools such as CA Clarity PPM, MS Project, SharePoint, Microsoft Office Suite, Rally, and other portfolio planning and financial management platforms.
• 4+ years’ operating effectively in ambiguous environments, resolving complex problems, and drive cross-functional decision-making.
• 4+ years’ experience implementing process improvement initiatives that increase efficiency, improve quality, reduce duplication of effort, and enhance team engagement.
• 2+ years demonstrated ability to balance strategic portfolio oversight with hands-on program leadership when required.
• PMP (Project Management Professional) or Certified ScrumMaster (CSM) certification or equivalent Agile certification.

Preferred Qualifications

• Established relationships with healthcare business leaders and technology stakeholders that support collaboration and organizational change initiatives.
• Previous leadership experience within a PMO environment as a Portfolio Manager, Program Manager, or PMO leader overseeing complex enterprise portfolios.
• Extensive knowledge of healthcare industry operations, regulatory requirements, IT systems, networks, applications, and compliance considerations.
• Expertise in product operating models, Agile portfolio management, roadmap development, and value stream planning.
• Strong negotiation, financial management, and executive-level decision-support capabilities.
• Demonstrated success mentoring and developing delivery leaders, program managers, and portfolio managers.
• Experience supporting hybrid and remote delivery organizations across multiple geographic locations.

Education

• Bachelor’s degree in computer science, Business Management, Information Technology, or a related field required.
• Master's degree preferred.
• Equivalent combination of education, specialized training, certifications, and relevant professional experience will be considered.

Pay Range

The typical pay range for this role is:

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.

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

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