Executive Assistant – Operations

Paired

Executive Assistant supporting a fast-moving entrepreneur with multiple businesses in Latin America. Managing calendars, guest communications, and property operations for diverse initiatives.

Posted 4/17/2026full-timeRemote • 🇨🇴 ColombiaMid-LevelSeniorWebsite

About the role

Key responsibilities & impact

Manage a complex, multi-business calendar across the EST time zone with LATAM overlap
Coordinate meetings, priorities, and schedule changes efficiently
Handle guest communications via booking platforms
Respond to inquiries promptly and professionally
Convert inquiries into confirmed bookings
Schedule and follow up with contractors (e.g., maintenance, gardening)
Coordinate service visits and block calendars accordingly
Ensure smooth day-to-day property operations
Oversee personal and household logistics connected to rental operations
Keep systems organized and running efficiently
Assist across multiple startup projects with ad-hoc tasks
Learn new tools quickly and execute new initiatives
Support general business operations as needed
Monitor booking platforms for occasional guest questions outside standard hours
Handle rare urgent issues (e.g., check-in problems, property incidents)

Requirements

What you’ll need

Proven experience as an Executive Assistant or in operations support, ideally for entrepreneurs or multi-business environments
Strong organizational and project management skills
Excellent written and verbal communication
Experience with calendar management tools (e.g., Google Calendar, time zone coordination)
Familiarity with booking platforms (e.g., Airbnb, Booking.com) or similar customer-facing systems
Experience using project management tools (e.g., Asana, ClickUp, Trello)
Proficiency in Google Workspace, especially Google Sheets for tracking and organization
Comfortable using communication tools (Slack, WhatsApp, email) for fast-paced coordination
Ability to multitask and prioritize in a dynamic environment
Proactive, resourceful, and detail-oriented
Fast learner with the ability to adapt to new tools and changing priorities
Comfortable with a flexible, on-call work model
**Nice to Have**
Experience with property management systems (PMS) like Guesty, Hostaway, or Hospitable
Background in short-term rentals or property management
Sales or negotiation skills (closing bookings, handling inquiries)
Exposure to marketing or digital tools (paid ads, analytics, etc.)

Benefits

Comp & perks

USD Salary.
Ability to work remotely.

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

calendar managementproject managementbooking platformsGoogle WorkspaceGoogle Sheetsproperty management systemssales skillsnegotiation skillsdigital marketing toolsanalytics

Soft Skills

organizational skillsproject management skillswritten communicationverbal communicationmultitaskingprioritizationproactiveresourcefuldetail-orientedadaptability