Executive Assistant to the CEO (Business Operations & Hospitality Focus)

Location: Remote (LATAM / South Africa / Philippines)
Schedule: Full-time, U.S. business hours
Reports To: CEO

About the Role

We’re seeking a proactive and highly organized Executive Assistant to the CEO who thrives in a fast-paced, entrepreneurial environment. This role combines business operations, hospitality coordination, and executive support — serving as the CEO’s right hand across a diverse portfolio of hotels, apartment complexes, and real estate investments.

You’ll help streamline operations, manage day-to-day execution, and implement systems that bring structure and efficiency to a growing organization. This is an opportunity to make a tangible impact by enabling the CEO to focus on high-leverage strategic work.

Key Responsibilities

Executive & Administrative Support

Act as the CEO’s trusted partner — managing inbox, calendar, travel, and priorities with discretion and accuracy.
Handle scheduling, meeting preparation, and follow-ups with attention to detail and clear communication.
Take initiative to anticipate needs, manage reminders, and ensure critical tasks are completed on time.

Business Operations & Project Management

Oversee daily workflows related to multiple business entities — including hotels, apartment complexes, and new real estate projects.
Support financial tracking, bookkeeping, and reporting using spreadsheets and accounting tools.
Monitor performance metrics and assist in preparing reports, rate sheets, and operational summaries.
Manage task and project systems to ensure smooth execution across all active business areas.

Property Management Support

Assist with property management software (e.g., CloudBeds, ResNexus) — including system transitions, data entry, and optimization.
Liaise with hotel managers, vendors, and service providers to ensure smooth day-to-day operations.
Research and implement operational improvements to increase guest satisfaction and efficiency.

Legal, Financial & Operational Coordination

Maintain organized documentation and filing systems for legal cases, financial statements, and contracts.
Support communications related to ongoing litigation and vendor relationships.
Coordinate with accountants, attorneys, and management companies as needed.

Technology & Automation

Research and implement new tools or AI solutions to enhance productivity and streamline operations.
Support the integration of software platforms across business units.

Ideal Candidate Profile

You are a solutions-oriented operator who thrives in ambiguity and takes ownership from day one. You’re equally comfortable creating a financial tracking sheet as you are managing a property management tool or following up on a vendor invoice.

Qualifications & Skills

3+ years of experience as an Executive Assistant, Business Operations Specialist, or similar role.
Experience supporting a CEO, Founder, or executive in a multi-entity environment preferred.
Strong understanding of business administration, property management, or hotel operations.
Highly proficient with spreadsheets (Google Sheets, Excel) and project management tools (Asana, ClickUp, Notion, etc.).
Comfortable learning and using hospitality management software (CloudBeds, ResNexus, or similar).
Strong organizational, written, and verbal communication skills in English.
Tech-savvy and adaptable — able to research, evaluate, and adopt new tools independently.
Familiarity with AI productivity tools (ChatGPT, Notion AI, Zapier, etc.) is a plus.

Personality & Work Style

Proactive and resourceful — anticipates needs before being asked.
Highly detail-oriented with strong follow-through and reliability.
Calm under pressure and able to prioritize effectively across competing demands.
A strong sense of ownership — treats the CEO’s success as their own.
Integrity, discretion, and professionalism when handling sensitive information.

Why Join

You’ll work directly with a visionary entrepreneur managing a fast-growing hospitality and real estate portfolio. This role is ideal for someone who loves variety, thrives in organized chaos, and wants to help build efficient systems from the ground up. Over time, this position will naturally evolve — offering growth opportunities into Operations Management, Business Strategy, or Portfolio Oversight based on your strengths.

Executive Assistant to CEO