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 Digital & 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 engine