Executive Assistant to CEO - 21457

Location: Fully remote Employment Type: Full-time Hours: U.S. Eastern business hours (approx. 9:00 AM – 6:00 PM ET), with flexibility to respond to time-sensitive matters during evenings or weekends when the executive is traveling.

We are a U.S.-based, vertically integrated hospitality investment and development firm, founded over a decade ago and headquartered in South Florida. We acquire, develop, and operate highly differentiated lifestyle and premium branded, full-service hospitality and real estate assets across North America.

Our advantage is entrepreneurial and hands-on. We move quickly, operate lean, and take on complex projects that others pass on — designing curated environments and delivering standout experiences for our guests, investors, and team. The pace is fast, the work is high-stakes, and the standard for execution is high.

This role exists to protect and extend the time of our CEO across both his professional and personal life. It is a single point of leverage: when this seat runs well, the CEO operates at full capacity and nothing slips.

Because the business runs on live deals, active travel, and frequent investor, partner, and internal communication, the standard here is meticulous, error-free execution. This is not a role for someone who needs step-by-step direction. We are looking for a sharp, fast-moving right hand who anticipates needs, catches problems before they surface, and takes true ownership of the details so the CEO doesn't have to.

You will work directly with the CEO, will occasionally support a second member of leadership on select business and personal matters, and will be trusted with sensitive information from day one.

Executive Support & Calendar Management

• →Own and manage a complex, frequently shifting calendar, resolving conflicts and protecting focus time.
• →Coordinate internal and external meetings across multiple time zones, ensuring the CEO is always prepared and on time.
• →Anticipate scheduling needs and proactively resolve competing priorities before they become issues.

Inbox & Communications Management

• →Monitor, triage, and help manage the executive inbox; surface what matters, draft responses, and ensure nothing goes unanswered.
• →Act as a polished, professional point of contact with investors, partners, vendors, and internal team members.
• →Manage timely follow-up so open items are tracked to completion.

Travel & Itinerary Management

• →Plan and book detailed domestic and international travel — flights, hotels, ground transport, and reservations.
• →Build clear, complete itineraries and adjust in real time when plans change, including outside standard hours during active travel.

Meeting & Document Preparation

• →Prepare agendas, briefing materials, and documents ahead of meetings.
• →Take notes, capture action items, and follow up to ensure commitments are executed.
• →Assist with expense reports, basic reporting, and light document preparation.

Personal & Lifestyle Support

• →Handle personal tasks for the CEO — appointments, reservations, personal travel, household or family coordination, and ad hoc requests.
• →Manage personal matters with the same discretion, care, and accuracy as business responsibilities.

Coordination & Project Follow-Through

• →Track cross-functional to-dos and keep projects moving on behalf of the CEO.
• →Serve as a reliable connective point between the CEO and the rest of the team.

• 4+ years of experience as an Executive Assistant supporting senior or C-level executives.
• Direct experience supporting U.S.-based companies and executives.
• A demonstrated track record of high-accuracy, near-zero-error execution — this is essential.
• Excellent written and verbal English communication.
• Availability to work full U.S. Eastern business hours, with flexibility for occasional off-hours responsiveness during executive travel.
• Strong proficiency with calendar, email, and productivity tools (Google Workspace and/or Microsoft 365, scheduling and travel tools).
• A reliable high-speed internet connection and a quiet, professional remote work environment.

• Background in real estate, hospitality, private equity, investment, or another fast-paced, deal-driven environment.
• Experience blending executive support with personal and lifestyle assistance.
• Experience supporting founders or entrepreneurial principals who operate at high speed.
• Experience supporting more than one stakeholder at the same time.

You are:

• Meticulous. You double-check your work, and things do not fall through the cracks. Accuracy is a point of pride.
• Fast and high-energy. You keep pace with a demanding executive and thrive when the day moves quickly.
• Highly intelligent and quick to learn. You pick up new tools, contexts, and preferences fast and rarely need to be told the same thing twice.
• Anticipatory. You see around corners and solve problems before they land on someone's desk.
• Discreet. You handle confidential business and personal matters with complete professionalism.
• Calm under pressure. Shifting priorities and last-minute changes don't rattle you.
• A true owner. You operate as a proactive partner, not an order-taker, and you take responsibility for outcomes