Executive Director, Health 100 Product & Engineering Chief of Staff

CVS Health is dedicated to building a world of health around every individual, prioritizing a connected and compassionate health experience. They are seeking an Executive Director, Health 100 Product & Engineering Chief of Staff to serve as a strategic advisor and enable sustained focus on the Health100 mission and product portfolio while navigating organizational challenges.

Responsibilities:

• Serve as a strategic advisor to the SVP, Health100 Chief Data & Technology Officer
• Enable sustained strategic focus, helping leaders stay aligned on what matters most
• Ensure the organization moves decisively in support of the Health100 mission and product portfolio
• Lead with a clear set of operating principles: outcomes over process, speed over business‑as‑usual, and mission over routine
• Keep leaders and teams focused on driving execution while delivering outcomes amid enterprise scale and complexity
• Act on behalf of the leadership team, navigating organizational and administrative obstacles to keep work moving forward
• Ensure clear and effective decision and information flows across product, engineering, design, and operations
• Escalate only those issues that materially impact portfolio vision, strategy, or execution for the Health100 Product & Engineering organization
• Bring strong judgment, ownership, and care to advancing Health100 with speed and discipline without unnecessary process

Requirements:

• 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