Executive Director, Health 100 Product & Engineering Chief of Staff

CVS Health•Woonsocket, IL

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. 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.

Requirements

15+ years of experience in a technology environment.
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.
Proven experience serving as a neutral broker and trusted thought partner to senior executives.
Strong strategic planning and cross-functional coordination skills.
Ability to distinguish between issues that require executive attention and those that can and should be resolved at a lower level.
Excellent written and verbal communication skills.
Proven ability to operate in complex, multi-stakeholder environments.
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.
Proven ability to thrive in a fast-moving, fast-evolving, startup-like environment inside a large enterprise.
Ability to work with significant autonomy, maintaining strong ownership, accountability, and execution rigor.

Nice To Haves

Deep care for the product and the members it serves.
Dedicated to the mission over routine.
Skilled at navigating administrative obstacles to keep the team focused on what matters.
Biased toward outcomes over process, moving fast and effectively rather than defaulting to business-as-usual.
Pursuing goals without getting distracted by organizational churn.

Responsibilities

Serves as a strategic advisor to the SVP, Health100 Chief Data & Technology Officer.
Enables sustained strategic focus for the leadership team.
Ensures leaders stay aligned on priorities and the organization moves decisively in support of the Health100 mission and product portfolio.
Acts as a force multiplier for the leadership team, leading with principles of outcomes over process, speed over business-as-usual, and mission over routine.
Keeps leaders and teams focused on driving execution and delivering outcomes in a complex enterprise environment.
Navigates organizational and administrative obstacles to keep work moving forward.
Ensures clear and effective decision and information flows across product, engineering, design, and operations.
Escalates issues that materially impact portfolio vision, strategy, or execution for the Health100 Product & Engineering organization.
Brings strong judgment, ownership, and care to advancing Health100 with speed and discipline without unnecessary process.
Anticipates executive needs and acts as an empowered representative across a broad range of organizational topics.
Prepares correspondence, messaging, and talking points with minimal direction.
Serves as a neutral broker and trusted thought partner to senior executives.
Connects data and decision points across teams, clarifies decision space, and ensures the right leaders are making the right decisions at the right time.
Identifies decisions that need to be made, surfaces them to appropriate decision-makers, and monitors execution without driving outcomes personally.
Distinguishes between issues that require executive attention and those that can be resolved at a lower level, protecting leadership bandwidth.
Represents executive and organizational positions to leadership teams, the broader organization, and external stakeholders.
Operates in complex, multi-stakeholder environments, including navigating internal partner and client relationships with credibility and sound judgment.
Works collaboratively across product, engineering, design, and operations in fast-paced, cross-functional environments.
Manages multiple high-priority initiatives simultaneously.
Operates in a product-oriented model, understanding how engineering, product, and design partner to deliver customer and business value.
Thrives in a fast-moving, fast-evolving, startup-like environment inside a large enterprise.
Works with significant autonomy, maintaining strong ownership, accountability, and execution rigor.