Strategy Lead Jobs in Boston, MA

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 SUMMARY

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.

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 experience operating in complex, cross-functional environments with multiple stakeholders
• Deep understanding of modern product operating models, prioritization frameworks, and governance structures
• Experience with AI-driven or technology-forward product innovation preferred

PREFERRED QUALIFICATIONS

• 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

EDUCATION
Bachelor’s degree or, equivalent experience (HS diploma + 4 years relevant experience)

BUSINESS OVERVIEW
Bring your heart to CVS Health Every one of us at CVS Health shares a single, clear purpose: Bringing our heart to every moment of your health. This purpose guides our commitment to deliver enhanced human-centric health care for a rapidly changing world. Anchored in our brand — with heart at its center — our purpose sends a personal message that how we deliver our services is just as important as what we deliver. Our Heart At Work Behaviors™ support this purpose. We want everyone who works at CVS Health to feel empowered by the role they play in transforming our culture and accelerating our ability to innovate and deliver solutions to make health care more personal, convenient and affordable. We strive to promote and sustain a culture of diversity, inclusion and belonging every day. CVS Health is an affirmative action employer, and is an equal opportunity employer, as are the physician-owned businesses for which CVS Health provides management services. We do not discriminate in recruiting, hiring, promotion, or any other personnel action based on race, ethnicity, color, national origin, sex/gender, sexual orientation, gender identity or expression, religion, age, disability, protected veteran status, or any other characteristic protected by applicable federal, state, or local law. We proudly support and encourage people with military experience (active, veterans, reservists and National Guard) as well as military spouses to apply for CVS Health job opportunities.

Pay Range

The typical pay range for this role is:

$144,200.00 - $288,400.00

This pay range represents the base hourly rate or base annual full-time salary for all positions in the job grade within which this position falls. The actual base salary offer will depend on a variety of factors including experience, education, geography and other relevant factors. This position is eligible for a CVS Health bonus, commission or short-term incentive program in addition to the base pay range listed above. This position also includes an award target in the company’s equity award program.

Our people fuel our future. Our teams reflect the customers, patients, members and communities we serve and we are committed to fostering a workplace where every colleague feels valued and that they belong.

Great benefits for great people

We take pride in offering a comprehensive and competitive mix of pay and benefits that reflects our commitment to our colleagues and their families.

This full‑time position is eligible for a comprehensive benefits package designed to support the physical, emotional, and financial well‑being of colleagues and their families. The benefits for this position include medical, dental, and vision coverage, paid time off, retirement savings options, wellness programs, and other resources, based on eligibility.

Additional details about available benefits are provided during the application process and on Benefits Moments.

We anticipate the application window for this opening will close on: 08/28/2026

Qualified applicants with arrest or conviction records will be considered for employment in accordance with all federal, state and local laws.