Lead Director - Portfolio and Program Delivery

CVS Health•Woonsocket, MS

2d•Hybrid

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. Role Overview 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.

Requirements

10+ years leading Program Managers, agile (scrum) teams, and technology teams to deliver strategic technology products at scale.
Proven experience managing IT portfolios and delivering complex, multi-year programs in large-scale, matrixed organizations as well as budget exceeding $40M.
5+ years of experience as a people leader with direct reports
Proven experience building or significantly transforming portfolio governance and program management practices from the ground up.
Demonstrated ability to convert executive-level strategy and roadmaps into structured, actionable delivery plans across complex organizations.
Demonstrated ability to flex between strategic portfolio oversight and hands-on program management when circumstances require it.
Experience designing, implementing, and continuously improving program and portfolio governance structures.
Strong communication and executive presence; skilled at influencing up, down, and across the organization, including with senior executives.
High standards for quality, accountability, and stakeholder engagement, with a track record of driving results through others.
Comfort operating in ambiguous environments, connecting the dots across disparate efforts, and driving clarity and alignment among diverse stakeholders.
Familiarity with portfolio management and product model toolsets (e.g., Rally, roadmap tools, initiative planning tools, financial tracking) and a willingness to deepen that expertise.

Nice To Haves

Bachelor's degree preferred/specialized training/relevant professional qualification.

Responsibilities

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 and roadmaps into actionable, executable portfolio and program plans, including program charters, sequencing, prioritization, and delivery approaches.
Design and build portfolio governance structures from the ground up, establishing frameworks, processes, and operating cadences that enable scalable, consistent, and transparent program delivery.
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 delivery leads are managing risk effectively within their areas.
Coordinate cross-functional responses to issues that threaten timeline, budget, scope, or quality, ensuring that decisions are made with appropriate speed and stakeholder involvement.
Use data and structured analysis to recommend tradeoffs and recovery plans when programs deviate from plan.
Foster a culture of continuous improvement, transparency, accountability, and collaboration across program and delivery teams.
Develop and mentor delivery managers and program leaders, helping them grow in areas such as planning, stakeholder management, communication, and risk management.
Encourage teams to adopt product model toolsets and best practices, including Rally (or similar tools), road mapping, initiative execution plans, and budget tracking.
Role model behaviors that emphasize partnership, clarity, and follow-through.