Lead Director, Agile Practice Management

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.

We are seeking an accomplished IT leader to serve as Director, IT Portfolio & Program Delivery. This is a high-impact leadership position responsible for overseeing a diverse, strategically important portfolio of technology initiatives and ensuring the highest standards of delivery, governance, and organizational alignment.

In this role, you will lead and support multiple, concurrent programs totaling 500,000+ hours of work and representing $40M of annual investment. You will be responsible for connecting business strategy to execution, creating structure and predictability in how work gets done, and ensuring that program outcomes translate into tangible value for the enterprise. Success in this role requires a rare combination of portfolio thinking, hands‑on program delivery expertise, and strong stakeholder leadership across technology and business partners.

• Portfolio Ownership and Strategy

• Own and manage a portfolio of multiple, concurrent programs totaling 500,000+ hours of effort and $40M in annual investment, ensuring alignment to enterprise and business‑unit strategies.

• Translate high‑level strategic objectives into a coherent portfolio roadmap, including program charters, sequencing, and prioritization across initiatives.

• Partner with technology and business leaders to define success criteria, expected outcomes, and value realization plans for major programs in the portfolio.

• Continuously assess portfolio health, balancing risk, capacity, dependencies, and value delivered; recommend adjustments to scope, sequencing, or resourcing as needed.

• Lead, monitor, and support delivery managers and program teams to achieve portfolio and program goals—providing guidance, feedback, coaching, and accountability.

• Step in directly to manage complex or high‑profile programs or projects when needed, ensuring successful delivery from initiation through closure, including planning, execution, and transition to run.

• Ensure that all programs in the portfolio operate with clear plans, defined deliverables, and measurable outcomes; establish expectations for planning horizons, milestone management, and risk mitigation.

• Promote disciplined execution practices across teams, including effective backlog management, dependency management, and change control.

• Establish, refine, and maintain program and portfolio governance frameworks, including roles, decision rights, approval thresholds, reporting cadence, and escalation protocols.

• Standardize core program and project management practices across teams, with clear templates and expectations for status reporting, RAID (Risks, Assumptions, Issues, Dependencies) tracking, and stakeholder communication.

• Drive adoption of consistent metrics and KPIs to track progress, quality, financial performance, and value realization across the portfolio.

• Partner with central PMO, Product, Business and Technology stakeholders to align on methodologies, standards, and reporting expectations.

• Lead portfolio status reporting and executive communications; provide clear, concise, and actionable updates to senior leadership, highlighting progress, risks, decisions, and tradeoffs.

• Build strong relationships with business owners, product leaders, and technology partners to ensure shared understanding of priorities, timelines, and constraints.

• Anticipate and proactively surface cross‑program dependencies and impacts; drive collaborative solutions across teams and functions to keep the portfolio on track.

• Serve as a thought partner on portfolio‑level decisions, including which initiatives to start, slow down, stop, or scale based on capacity, risk, and strategic value.

• Identify risks early, anticipate roadblocks, and implement mitigation strategies across programs; ensure that