Chief of Staff

Chewy • Plantation, FL

1d

About The Position

Our Opportunity Chewy is seeking a Chief of Staff to support the President of Chewy Health. This is a highly visible role responsible for driving clarity, alignment, and execution across one of Chewy’s most strategic and complex growth businesses. As a trusted advisor and operational partner to the President, this leader will help shape and operationalize Chewy Health’s strategy while ensuring disciplined execution against key priorities. The Chief of Staff will develop a comprehensive understanding of Chewy’s healthcare ecosystem—including pharmacy, clinical services, regulatory considerations, partnerships, product, and customer experience—and translate strategy into structured plans, measurable outcomes, and scalable operating mechanisms. This role requires strong business judgment, operational rigor, executive presence, and the ability to navigate complexity in a fast-paced, regulated environment. The ideal candidate is both framework-oriented and execution-focused—equally comfortable advising at the strategic level and driving cross-functional initiatives to completion.

Requirements

• Bachelor’s degree in Business, Healthcare Administration, or related field
• 10+ years of experience in strategy, operations, healthcare, consulting, or business leadership roles
• Demonstrated success leading complex, cross-functional initiatives from strategy through execution
• Strong business and operational acumen, ideally within healthcare, pharmacy, or regulated industries
• Experience supporting senior executives in high-growth, matrixed environments
• Proven ability to build and scale operating mechanisms and performance management processes
• Exceptional written and verbal communication skills, including executive-level materials development
• Data-driven approach to prioritization, decision-making, and problem-solving
• Strong stakeholder management and influence skills across diverse teams
• Ability to anticipate future business needs and build proactive solutions

Nice To Haves

• MBA or advanced degree
• Experience in healthcare services, digital health, pharmacy, or regulated environments
• Senior leadership experience (Director+ level)
• Previous experience as a Chief of Staff or Technical Advisor
• Experience in high-growth, tech-enabled organizations

Responsibilities

• Serve as a trusted advisor and day-to-day thought partner to the President of Chewy Health.
• Help refine and articulate Chewy Health’s long-term strategy, ensuring alignment with enterprise priorities.
• Translate strategic direction into actionable roadmaps, measurable KPIs, and cross-functional plans.
• Prepare executive-level materials, board-ready content, business reviews, and decision frameworks.
• Organize and prioritize critical issues to enable effective, data-driven decision-making.
• Lead and coordinate high-priority, cross-functional initiatives from concept through delivery.
• Define scope, milestones, accountability structures, and success metrics for key programs.
• Identify risks, trade-offs, and interdependencies across clinical, pharmacy, product, operations, marketing, finance, and technology.
• Drive accountability and remove execution barriers to ensure on-time, high-quality outcomes.
• Establish and refine operating rhythms (leadership meetings, goal-setting processes, business reviews, planning cadences).
• Represent the President in meetings and forums as appropriate; manage pre-work, facilitate discussions, and ensure follow-through.
• Coordinate with external partners within the broader pet healthcare ecosystem when needed.
• Surface risks proactively and coordinate mitigation strategies.
• Identify structural or process gaps and implement scalable solutions.

Benefits

• Chewy is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, ancestry, national origin, gender, citizenship, marital status, religion, age, disability, gender identity, results of genetic testing, veteran status, as well as any other legally-protected characteristic.
• If you have a disability under the Americans with Disabilities Act or similar law, and you need an accommodation during the application process or to perform these job requirements, or if you need a religious accommodation, please contact [email protected].
• To access Chewy's California CPRA Job Applicant Privacy Policy, please click here.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Number of Employees: 5,001-10,000 employees