Lead Director, Strategy and Operations

CVS Health • Island, KY

3d • $100,000 - $231,540

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 As the Lead Director, Strategy and Operations for the Connected PBM Ecosystem, you will report to the Executive Director of Solution Delivery & Execution driving the effectiveness of the leadership team. You will be pivotal in communicating key messages, solving complex problems through collaboration and influence, and supporting key operational workstreams. This role supports the Connected PBM Ecosystem — a multi-workstream program integrating people, process, and technology to optimize enterprise value. This is truly a unique role offering exposure to each aspect of the PBM. You will build strong relationships across the PBM enterprise with senior stakeholders, ensuring priorities are clearly communicated. Key Responsibilities: Connected PBM Ecosystem and Enterprise Business Strategy Lead the annual strategic planning process, ensuring alignment with business objectives and rigorous KPI monitoring. Apply deep industry, customer and business acumen to anticipate trends, inform decisions, and drive competitive advantage. Lead special projects across the organization including executive-level presentations, innovation partnerships, return on investment (ROI) and impact reporting. Transform data and insights into compelling narratives and strategic points of view that influence decision-making. Demonstrate sound judgment in knowing when to ‘lead versus do’—providing strategic guidance and direction to teams, while leaning into hands-on execution when necessary to ensure quality and timely delivery. Executive Communication & Influence Communicate key messages ensuring information flow, clarity, and visibility across team, senior leaders and stakeholders through effective communication channels. Develop and execute strategies that showcase the value of activities, drive leadership engagement, and ensure organizational awareness of impact. Optimize leadership management routines and governance models to enhance decision-making and operational cadence. Influence outcomes in dynamic environments, demonstrating agility to pivot strategies and approaches as needed. Organizational Engagement & Culture Oversee departmental operations with attention to detail and follow through, including leading planning, budgeting, recruiting, and colleague performance review and promotion process. Provide leadership and oversight for one direct reports, including: performance management, professional development, and alignment to organizational goals. Provide strategic counsel to senior leaders and teams, fostering alignment and clarity on priorities. Drive colleague engagement initiatives, including analysis of engagement data and operationalization of action plans. Foster collaboration and a strong culture to support colleague engagement events, colleague onboarding, career development, and recruitment. Strategic Partnerships & Innovation Cultivate high-value partnerships (w/ key stakeholders) and alliances to expand capabilities, influence management routines, and unlock new growth opportunities. To be a candidate for this role you will possess the following: Adept at execution and delivery (planning, delivering, and supporting) skills Ability to translate executive vision into a compelling, engaging narrative and operational plan Skilled in managing cross-functional initiatives and driving results Comfortable with performance metrics, dashboards, and business intelligence tools Excellent interpersonal style, good listening skills and the ability to communicate highly complex ideas clearly and concisely Excellent planning, organizational, and time management skills Ability to implement new ideas and influence dynamic thinking Excellent analytical skills and ability to consume large quantities of information

Requirements

• Adept at execution and delivery (planning, delivering, and supporting) skills
• Ability to translate executive vision into a compelling, engaging narrative and operational plan
• Skilled in managing cross-functional initiatives and driving results
• Comfortable with performance metrics, dashboards, and business intelligence tools
• Excellent interpersonal style, good listening skills and the ability to communicate highly complex ideas clearly and concisely
• Excellent planning, organizational, and time management skills
• Ability to implement new ideas and influence dynamic thinking
• Excellent analytical skills and ability to consume large quantities of information
• 10+ years of prior work experience
• 5+ years in leadership roles including planning, budgeting, recruiting, performance and culture
• 5+ years acting as a content architect for executive forums—translating complex program updates into concise, strategic narratives
• Experience managing cross-functional initiatives and driving results
• Experience impacting and influencing key stakeholders across the organization (up, down and across)
• Experience presenting to senior leaders and facilitating discussions in a dynamic environment

Nice To Haves

• Healthcare experience
• Master’s or MBA preferred

Responsibilities

• Lead the annual strategic planning process, ensuring alignment with business objectives and rigorous KPI monitoring.
• Apply deep industry, customer and business acumen to anticipate trends, inform decisions, and drive competitive advantage.
• Lead special projects across the organization including executive-level presentations, innovation partnerships, return on investment (ROI) and impact reporting.
• Transform data and insights into compelling narratives and strategic points of view that influence decision-making.
• Demonstrate sound judgment in knowing when to ‘lead versus do’—providing strategic guidance and direction to teams, while leaning into hands-on execution when necessary to ensure quality and timely delivery.
• Communicate key messages ensuring information flow, clarity, and visibility across team, senior leaders and stakeholders through effective communication channels.
• Develop and execute strategies that showcase the value of activities, drive leadership engagement, and ensure organizational awareness of impact.
• Optimize leadership management routines and governance models to enhance decision-making and operational cadence.
• Influence outcomes in dynamic environments, demonstrating agility to pivot strategies and approaches as needed.
• Oversee departmental operations with attention to detail and follow through, including leading planning, budgeting, recruiting, and colleague performance review and promotion process.
• Provide leadership and oversight for one direct reports, including: performance management, professional development, and alignment to organizational goals.
• Provide strategic counsel to senior leaders and teams, fostering alignment and clarity on priorities.
• Drive colleague engagement initiatives, including analysis of engagement data and operationalization of action plans.
• Foster collaboration and a strong culture to support colleague engagement events, colleague onboarding, career development, and recruitment.
• Cultivate high-value partnerships (w/ key stakeholders) and alliances to expand capabilities, influence management routines, and unlock new growth opportunities.

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