Lead Director – Portfolio and Program Delivery

CVS Health

Director of IT Portfolio & Program Delivery overseeing technology initiatives worth $40M+. Leading program management teams to ensure strategic alignment and delivery excellence.

Posted 5/14/2026full-timeWoonsocket • Louisiana, Mississippi, North Carolina, Rhode Island • 🇺🇸 United StatesSenior💰 $144,200 - $288,400 per yearWebsite

About the role

Key responsibilities & impact

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

Requirements

What you’ll need

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.

Benefits

Comp & perks

medical, dental, and vision coverage
paid time off
retirement savings options
wellness programs
comprehensive benefits package

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

program managementportfolio managementagilescrumrisk mitigationbudget managementstrategic planningstakeholder communicationgovernance frameworksdelivery planning

Soft Skills

leadershipcommunicationinfluencingaccountabilityproblem-solvingadaptabilitycollaborationcoachingexecutive presencestakeholder engagement