Executive Director, Health 100 Product & Engineering Chief of Staff

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. As a key member of the Health100 Product & Engineering leadership ecosystem, the Chief of Staff serves as a strategic advisor to the SVP, Health100 Chief Data & Technology Officer. This highly visible role exists to enable sustained strategic focus, helping leaders stay aligned on what matters most and ensuring the organization moves decisively in support of the Health100 mission and product portfolio. Operating as a force multiplier for the leadership team, the Chief of Staff leads with a clear set of operating principles: outcomes over process, speed over business‑as‑usual, and mission over routine. Operating in a fast‑moving, startup‑like environment inside a large enterprise, the role keeps leaders and teams focused on driving execution while delivering outcomes amid enterprise scale and complexity. The Chief of Staff acts on behalf of the leadership team, navigating organizational and administrative obstacles to keep work moving forward, ensuring clear and effective decision and information flows across product, engineering, design, and operations, and escalating only those issues that materially impact portfolio vision, strategy, or execution for the Health100 Product & Engineering organization. Deeply invested in the product and its users, the role brings strong judgment, ownership, and care to advancing Health100 with speed and discipline without unnecessary process. Required Qualifications 15+ years of experience in a technology environment, including at least 5 years in a senior leadership role influencing enterprise-level strategy and business decisions. Demonstrated ability to anticipate executive needs and act as an empowered representative across a broad range of organizational topics, including preparing correspondence, messaging, and talking points with minimal direction. Proven experience serving as a neutral broker and trusted thought partner to senior executives — connecting data and decision points across teams, clarifying decision space, and ensuring the right leaders are making the right decisions at the right time. Strong strategic planning and cross-functional coordination skills, with the ability to identify decisions that need to be made, surface them to appropriate decision-makers, and monitor execution without driving outcomes personally. Ability to distinguish between issues that require executive attention and those that can and should be resolved at a lower level — actively protecting leadership bandwidth for external and strategic priorities. Excellent written and verbal communication skills, with demonstrated ability to represent executive and organizational positions to leadership teams, the broader organization, and external stakeholders. Proven ability to operate in complex, multi-stakeholder environments, including navigating internal partner and client relationships with credibility and sound judgment. Highly collaborative leader comfortable working across product, engineering, design, and operations in fast-paced, cross-functional environments. Demonstrated success managing multiple high-priority initiatives simultaneously, with strong project management, prioritization, and organizational skills and exceptional attention to detail. Experience operating in a product-oriented model, with a strong understanding of how engineering, product, and design partner to deliver customer and business value, including a deep care for the product and the members it serves. Proven ability to thrive in a fast-moving, fast-evolving, startup-like environment inside a large enterprise — dedicated to the mission over routine, and skilled at navigating administrative obstacles to keep the team focused on what matters. Ability to work with significant autonomy, maintaining strong ownership, accountability, and execution rigor - biased toward outcomes over process, moving fast and effectively rather than defaulting to business-as-usual, and pursuing goals without getting distracted by organizational churn. Pay Range The typical pay range for this role is: $131,500.00 - $303,195.00 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: 07/31/2026 Qualified applicants with arrest or conviction records will be considered for employment in accordance with all federal, state and local laws. Our Work Experience is the combination of everything that's unique about us: our culture, our core values, our company meetings, our commitment to sustainability, our recognition programs, but most importantly, it's our people. Our employees are self-disciplined, hard working, curious, trustworthy, humble, and truthful. They make choices according to what is best for the team, they live for opportunities to collaborate and make a difference, and they make us the #1 Top Workplace in the area.