Director, Strategic Planning

CVS Health • Woonsocket, RI

3d

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. Position Summary The Director of Strategic Planning leads a centralized planning team responsible for building, aligning, and activating the strategy for the Retail Pharmacy organization. This leader oversees a team of 5–7 and reports to the Chief of Staff & Executive Director, Strategic Planning & Business Operations. This role will have a balance of strategy development, enterprise partnerships communication, and leadership support for special projects like annual planning, store visit coordination, and initiative execution.

Requirements

• Bachelor’s degree in Business, Strategy, Economics, or related field required
• 10+ years of experience in management consulting, retail, or health care industry, including 5+ years in a people‑leadership role.
• Demonstrated experience building enterprise‑level strategic plans and facilitating senior‑level planning and business reviews.
• Strong analytical and problem‑solving skills, with the ability to synthesize complex information into clear recommendations.
• Excellent communication, storytelling, and executive‑level presentation skills and the ability to lead with agility and through ambiguity to influence in a matrixed environment.

Responsibilities

• Strategic Planning & Multi‑Year Road mapping Coordinate annual & multi-year planning to align interests of enterprise stakeholders, Retail Pharmacy business teams, and key partners like technology, marketing, operations, and finance.
• Define, centralize, and maintain the organization’s multi‑year strategy across business, strategy, and partner teams.
• Lead creation and monthly refresh of the consolidated strategic plan, including goals, business unit strategies, execution plans, and performance updates.
• Business Reviews & Performance Assessment Orchestrate monthly and quarterly business reviews to evaluate performance against goals and adjust year‑to-go plans as needed.
• Provide executive‑ready insights, recommendations, and decision support across Retail Pharmacy.
• Enterprise & Market Insights Monitor external trends and conduct strategic assessments to identify risks, opportunities, and emerging areas for growth.
• Partner with enterprise teams to maintain strong cross‑organizational relationships and surface collaboration opportunities.
• Strategic Initiatives & Special Projects Execute or provide consulting support for strategic projects (e.g., small box, onsite, asynchronous condition bundles).
• Support measurement frameworks and evaluation of key retail initiatives.
• Communications & Strategic Alignment Drive communications that unify organization's strategic direction, including developing presentations for executives and partnering business units.
• Identify and maintain channels and partnerships to ensure consistent and scalable strategy cascade across the organization (e.g., newsletters, field communications, earnings calls).
• Leadership & Team Development Lead and develop a high‑performing Strategic Planning team consisting of 5-7 colleagues, fostering a culture of collaboration, curiosity, and disciplined execution.
• Serve as a trusted advisor to senior leadership, helping connect strategy to execution and align teams toward shared outcomes.

Benefits

• Affordable medical plan options, a 401(k) plan (including matching company contributions), and an employee stock purchase plan.
• No-cost programs for all colleagues including wellness screenings, tobacco cessation and weight management programs, confidential counseling and financial coaching.
• Benefit solutions that address the different needs and preferences of our colleagues including paid time off, flexible work schedules, family leave, dependent care resources, colleague assistance programs, tuition assistance, retiree medical access and many other benefits depending on eligibility.

What This Job Offers

• Job Type: Full-time
• Career Level: Director