Chief of Staff to the CEO

Chief of Staff to the CEO

This role is eligible for our hybrid work model: 2 days in-office

The Chief of Staff will play a critical role in helping the CEO scale leadership, sharpen focus, and drive results. This position offers unique exposure to company-wide strategy and executive decision-making, making it an exceptional opportunity for a proven low-ego leader looking to have outsized impact.

Why this job’s a big deal:

The Chief of Staff to the CEO is a force multiplier for the CEO acts as the "connective tissue" for the executive team. This role is designed to maximize the CEO’s impact and effectiveness by protecting leadership focus, managing the company’s operating rhythm, driving cross-departmental alignment, accelerating execution, and ensuring follow-through on the company’s most critical priorities.

This is not an administrative role. The CEO will continue to have a dedicated Executive Assistant responsible for calendar, logistics, and travel. The Chief of Staff focuses on strategy, execution, decision support, and organizational leverage.

The ideal candidate brings strong business judgment, exceptional communication skills, and the ability to move seamlessly between strategy and hands-on execution.

In this role you will get to:

Operating Rhythm & Execution

• Drive the CEO’s operating cadence (e.g., leadership meetings, quarterly business reviews, offsites). You are responsible for the agenda, ensuring pre-read materials are distributed, and capturing and tracking all action items to completion.

• Work with senior leaders to translate company priorities into clear plans, with defined owners, milestones, and metrics. 

• Track execution against top initiatives and proactively flag risks, dependencies, or misalignment. 

Cross-Functional Alignment

• Ensure every department’s goals are documented and that status updates are accurate and timely.

• Partner with executives and senior leaders to ensure alignment across functions.

• Help resolve cross-functional friction and unblock decision-making. Serve as a connective tissue across the leadership team without becoming a bottleneck.

Special Projects & Priority Initiatives

• Lead or support high-impact, CEO-sponsored initiatives (e.g., organizational changes, new operating models, transformation efforts).

• Stand up structure where none exists and bring clarity to ambiguous problems.

• Own end-to-end execution for select initiatives, from definition through delivery.
   

Communication

• Prepare the CEO for important meetings. Own the production of concise briefs, key information and analysis, and high-quality presentations, including Board materials.

• Help craft and reinforce the CEO’s narrative internally and externally, and support preparation for company-wide communications, leadership forums, and all important company meetings (in partnership with the Communications team).

Who you are:

Experience & Background

• 8–15+ years of experience in strategy, operations, consulting, or project management roles

• Experience working closely with senior executives and navigating complex organizations

• Strong business and financial acumen; expert with data and metrics

• Proven experience leveraging GenAI as a force multiplier (for operational efficiency, research, high quality thought partnering, idea generation, etc.)
   

Skills & Capabilities

• Exceptional written and verbal communication

• Ability to synthesize complex data and information into clear insights and actions

• High judgment, discretion, and emotional intelligence

• Able to operate effectively with influence rather than authority

• Comfortable operating with ambiguity and in fast-changing environments

• Bias for action with strong follow-through
   

Personal Attributes

• Trusted, low-ego, and highly collaborative

• Proactive and anticipates needs before they arise

• Calm under pressure; confident working on sensitive matters

• Oriented toward impact, not visibility

• Illustrated history of living the values necessary to Priceline: C