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

Position: Lead Director - Product Office Strategy & Stakeholder Management (Retail Pharmacy Tech)
Location: Gassaway

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.

POSITION SUMMARYCVS 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 Health
100 (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.

Expectations for the Role End-to-End Product Strategy & Roadmap Ownership 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

OKR Definition, Alignment & Value Tracking 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

Product Office Leadership (Operating Model & Governance)
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

Strategic Communications & Storytelling 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

Cross-Functional Leadership & Alignment 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

REQUIRED QUALIFICATIONS
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…