Executive Director, Health 100 Product & Engineering Chief of Staff

CVS Health•Woonsocket, IL

13d•$131,500 - $303,195

About The Position

The Chief of Staff is a strategic advisor to the SVP, Health100 Chief Digital & Technology Officer and a key member of the Health100 Product & Engineering leadership ecosystem. The role enables sustained strategic focus by helping leaders stay aligned on priorities and ensuring the organization advances the Health100 mission and product portfolio decisively. Operating as a force multiplier for the leadership team in a fast-moving, startup-like environment within a large enterprise, the Chief of Staff keeps leaders and teams focused on execution and outcomes. The role acts on behalf of the leadership team to navigate organizational and administrative obstacles, maintain effective decision and information flows across product, engineering, design, and operations, and escalate issues that materially affect portfolio vision, strategy, or execution. It requires strong judgment, ownership, and care for the product and its users, while advancing Health100 with speed and discipline without unnecessary process. This full-time role offers a typical base pay range of $131,500 to $303,195 and is eligible for a CVS Health bonus, commission or short-term incentive program, as well as an equity award target. The benefits package includes medical, dental, and vision coverage, paid time off, retirement savings options, wellness programs, and other resources, based on eligibility.

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.
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.
Experience serving as a neutral broker and trusted thought partner to senior executives, connecting data and decision points across teams and clarifying decision space.
Strong strategic planning and cross-functional coordination skills, including identifying decisions, surfacing them to appropriate decision-makers, and monitoring execution without driving outcomes personally.
Ability to distinguish between issues requiring executive attention and those that can be resolved at a lower level, protecting leadership bandwidth for external and strategic priorities.
Excellent written and verbal communication skills, including the ability to represent executive and organizational positions to leadership teams, the broader organization, and external stakeholders.
Ability to operate in complex, multi-stakeholder environments and navigate internal partner and client relationships with credibility and sound judgment.
Collaborative leadership skills and comfort 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 in a product-oriented model and strong understanding of how engineering, product, and design partner to deliver customer and business value.
Ability to thrive in a fast-moving, fast-evolving, startup-like environment within a large enterprise and navigate administrative obstacles to keep the team focused on its mission.
Ability to work with significant autonomy, ownership, accountability, and execution rigor, with a bias toward outcomes over process.

Responsibilities

Serve as a strategic advisor to the SVP, Health100 Chief Digital & Technology Officer.
Help leaders maintain strategic focus and alignment on priorities for the Health100 mission and product portfolio.
Act as a force multiplier for the leadership team, supporting execution and outcomes in a fast-moving, startup-like environment within a large enterprise.
Represent the leadership team in navigating organizational and administrative obstacles so work continues to move forward.
Ensure clear and effective decision and information flows across product, engineering, design, and operations.
Escalate issues that materially affect portfolio vision, strategy, or execution.
Connect data and decision points across teams, clarify decision space, and help ensure the appropriate leaders make decisions at the appropriate time.
Identify decisions that need to be made, surface them to appropriate decision-makers, and monitor execution without personally driving outcomes.
Distinguish issues requiring executive attention from those that can be resolved at a lower level, protecting leadership bandwidth for external and strategic priorities.
Prepare executive correspondence, messaging, and talking points with minimal direction.
Represent executive and organizational positions to leadership teams, the broader organization, and external stakeholders.
Coordinate across internal partners and clients in complex, multi-stakeholder environments.
Manage multiple high-priority initiatives while maintaining prioritization, organization, and attention to detail.