Chief of Staff

Fort Lauderdale, FL

Full-time

1001-5000

Series B・$20M

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🔴 Closes on:

Sep 27, 2025

Job Description:

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.