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.

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.

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.

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