Lead Director - Product Office Strategy & Stakeholder Management (Retail Pharmacy Tech)

CVS Health•Woonsocket, MS

11d•$144,200 - $288,400

About The Position

CVS Health Digital is looking for hands-on, passionate people who want to join a high energy and growing team to make a difference in customers’ lives and who want to be on the forefront of digital innovation that aims to reinvent what a pharmacy and a health care company can be in the digital world. The Lead Director - Product Office Strategy & Stakeholder Management (Retail Pharmacy Tech) will serve as a key leader in shaping and driving the end-to-end strategy, roadmap, and execution discipline for Retail Pharmacy Technology. This role is accountable for translating business priorities across CVS Retail Pharmacy and the Health100 (H100) ecosystem into a cohesive, outcome-driven product strategy. This leader will operate at the intersection of product, business, and engineering to ensure that investments are aligned to value, progress is measurable, and impact is clearly communicated through compelling, executive-level storytelling.

Requirements

10+ years of experience in product strategy, product management, or portfolio leadership, preferably in healthcare or retail technology
Proven track record of building and managing large-scale product roadmaps and portfolios
Experience driving OKRs, value measurement frameworks, and executive reporting
Strong ability to create executive-level communications and compelling product narratives
Demonstrated experience operating in complex, cross-functional environments with multiple stakeholders
Deep understanding of modern product operating models, prioritization frameworks, and governance structures
Bachelor’s degree or, equivalent experience (HS diploma + 4 years relevant experience)

Nice To Haves

Experience with AI-driven or technology-forward product innovation preferred
Experience with Retail Pharmacy industry preferred
Experience operating in highly regulated or complex enterprise environments
Ability to determine strategy along with the plans, which need to be implemented to meet the end goal, evaluating situations, decisions, and issues in the short, medium, and long term
In depth experience in Agile development methodologies
Individually motivated to be able to see the big picture and prioritize their work to make the largest impact on the business and customers vision and requirements
Influence and persuade - able to present sound and well-reasoned arguments to convince others. Adapt to the situation and can draw from a range of strategies to persuade people in a way that results in agreement or behavior change
Track record of driving cross‑functional change and technology adoption

Responsibilities

Own and continuously evolve the enterprise-scale roadmap for Retail Pharmacy Technology products and features
Ensure alignment of roadmap to business priorities, value streams, and partner outcomes across CVS Retail Pharmacy and the H100 ecosystem
Drive clarity on investment trade-offs, sequencing, and value realization across the portfolio
Partner closely with Product, Engineering, and Business leaders to ensure roadmap execution translates into measurable impact
Collaborate with business and operations leaders to define OKRs across key value streams
Establish a consistent framework to track progress, measure outcomes, and report value realization
Drive discipline in linking product delivery → business outcomes → financial and operational impact
Ensure transparent, data-driven reporting of performance against commitments
Own and lead the Product Office function for Retail Pharmacy Technology
Define and manage intake, prioritization, and portfolio governance processes across multiple product portfolios
Create a structured, scalable intake model to evaluate incoming requests against strategic priorities and capacity
Lead cross-portfolio prioritization discussions to ensure focus on highest-value initiatives
Bring consistency and rigor to ways of working, planning cycles, and execution governance
Lead development of executive-ready narratives and materials that communicate the impact of Retail Pharmacy Technology investments
Create compelling stories showcasing AI-native, tech-forward innovation and its impact on pharmacy workflows, patient care, and operational efficiency
Prepare leadership communications including business reviews, board-level materials, and executive updates
Ensure messaging clearly connects product capabilities → business outcomes → strategic differentiation
Act as a connector across Product, Engineering, Business, and Operations to drive alignment on strategy and execution
Enable leadership teams with clear insights, priorities, and decision frameworks
Drive a culture of ownership, accountability, and outcome orientation across value streams