Executive Assistant (Operations) For a USA Client - Remote

Paired is a global staffing and recruiting agency that specializes in pairing remote work with top-tier talent. We admire the importance of innovative social media strategies and are committed to connecting talented individuals with great companies that need their unique skills. Our mission is to provide great jobs to talented people, no matter where they are located.

We’re looking for a highly organized and proactive Executive Assistant in Latin America to support a fast-moving entrepreneur managing multiple businesses, including short-term rental operations and startup projects.

You’ll act as a key operator, owning calendars, coordinating property operations, supporting business initiatives, and stepping in where needed to keep everything running smoothly.

Key Responsibilities

Calendar & Schedule Management

• Manage a complex, multi-business calendar across the EST time zone with LATAM overlap
• Coordinate meetings, priorities, and schedule changes efficiently

Short-Term Rental Operations

• Handle guest communications via booking platforms
• Respond to inquiries promptly and professionally
• Convert inquiries into confirmed bookings

Property Management Coordination

• Schedule and follow up with contractors (e.g., maintenance, gardening)
• Coordinate service visits and block calendars accordingly
• Ensure smooth day-to-day property operations

Household & Logistics Management

• Oversee personal and household logistics connected to rental operations
• Keep systems organized and running efficiently

Startup & Operations Support

• Assist across multiple startup projects with ad-hoc tasks
• Learn new tools quickly and execute new initiatives
• Support general business operations as needed

On-Call Availability

• Monitor booking platforms for occasional guest questions outside standard hours
• Handle rare urgent issues (e.g., check-in problems, property incidents)
• This is a low-volume but important responsibility

Work Structure

• 40 hours/week (Monday–Friday) with flexibility (split shifts possible)
• On-call component for occasional urgent matters outside standard hours
• Workload may vary week-to-week depending on business needs
• 1–4 week paid trial period before long-term commitment

Requirements

• 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

• USD Salary.
• Ability to work remotely.