At Vacatia, we’re transforming how people vacation and how executive leadership powers that transformation. As a leading hospitality company, we combine data, technology, and personalized service to create unforgettable vacation experiences across our growing portfolio of resorts. Now, we’re seeking a Chief of Staff to the CEO, a strategic partner and operational powerhouse who will help steer our company through its next phase of growth, innovation, and organizational scale.

Why You’ll Love Working at Vacatia

• Strategic Access: Work side-by-side with a visionary CEO and help drive top company priorities, acquisitions, board communications, and organizational alignment.

• Cross-Functional Influence: Collaborate with teams across operations, finance, people, marketing, and technology and connect the dots between strategy and execution.

• High-Impact Leadership: Own the rhythm of the business: lead strategic planning, board preparation, business reviews, and cross-functional initiatives.

• A Company on the Rise: Join a mission-driven, growth-focused organization that values forward thinking, data-driven decisions, and smart tools including AI-driven innovation.

Your Impact

• Serve as the CEO’s right hand by tracking strategic priorities, driving alignment, and ensuring high-level initiatives are executed across the organization.

• Lead the cadence of executive meetings, strategic planning sessions, board presentations, and business reviews.

• Represent the CEO in meetings and communications as needed, and ensure follow-up, accountability, and momentum on key projects.

• Partner with Finance and Operations to monitor company performance, surface insights, and identify areas for improvement.

• Own and manage cross-functional projects related to growth, acquisitions, investor relations, people strategy, and internal systems.

• Build scalable systems, documentation, and processes that streamline executive operations and improve organizational clarity.

• Evaluate and implement AI-driven tools and insights to support business decisions, improve operational efficiency, and enhance the CEO’s ability to lead with data.
  

What You Bring

• 7+ years of experience in strategic operations, Chief of Staff roles, consulting, or senior business advisory positions.

• Bachelor’s degree required; MBA or similar advanced degree preferred.

• Experience in fast-paced, high-growth, or PE-backed environments; hospitality or service industry background preferred.

• Proven track record supporting executive leadership and preparing high-stakes materials for board-level audiences.

• Proven ability to independently access and analyze data, ideally with proficiency in SQL or similar querying languages; an engineering, technical, or analytical background is a strong plus

• Excellent communication skills in verbal, written, and interpersonal with strong executive presence and emotional intelligence.

• Demonstrated ability to manage multiple initiatives, work cross-functionally, and influence without authority.

• Experience with AI or automation tools in a business context whether evaluating, implementing, or collaborating on adoption.

• High integrity, discretion, business acumen, and operational rigor.

Be Part of Something Bigger

If you're ready to bring your strategic mind, operational expertise, and executive polish to a company in growth mode, we want to hear from you.

Apply today and help Vacatia shape the future of vacations from the top.