Executive Assistant (Travel & Calendar Management)

We’re looking for an Executive Assistant who is deeply detail-oriented, calm under pressure, and exceptional at booking and managing complex travel. You’ll be supporting a well-known comedian, handling all flights, calendars, itineraries, and last-minute adjustments that come with a high-velocity schedule.

This role is ideal for someone who thrives on precision, logistics, and solving problems before they happen. If you love making chaos feel controlled and can manage travel with zero room for error, you’ll be a strong fit.

Why You’ll Want to Join

• Paid in USD (bi-monthly: 15th and 30th)
• Up to 14 days of Paid Time Off annually
• Observance of Holidays based on your location
• 100% remote setup with flexibility to work where you perform best
• Work directly with a high-profile client operating in entertainment
• Build and manage a mission-critical travel and scheduling system from the ground up

What You’ll Work On

Flight Booking & Travel Coordination

• Book, manage, and update daily flights for a famous comedian across tours, shows, press events, and last-minute engagements
• Compare routes, airline policies, pricing, luggage restrictions, and timing for the absolute best option
• Create clean, accurate itineraries with all confirmations, backup plans, and timing buffers
• Monitor flights proactively and handle delays, cancellations, or re-routes in real time

Calendar & Schedule Management

• Own a constantly moving, high-complexity calendar with complete accuracy
• Coordinate show schedules, travel windows, meetings, rehearsals, and personal commitments
• Communicate schedule updates clearly and ahead of time
• Ensure no conflicts, overlaps, or timing risks

Day-to-Day Executive Assistance

• Manage logistics, reminders, checklists, and time-sensitive updates
• Communicate with managers, agents, tour staff, venues, and assistants
• Maintain clear documentation and systems for travel history, receipts, and preferences
• Anticipate needs before they are stated and resolve problems quickly

What You Bring

• 3+ years as an Executive Assistant, Travel Coordinator, or similar logistics-heavy role
• Expert-level travel booking experience (international + domestic)
• Mastery of Google Calendar and complex scheduling workflows
• Strong written and verbal communication
• Unmatched attention to detail — accuracy is everything in this role
• Ability to work fast, adjust quickly, and stay organized under pressure
• Comfort handling confidential information and high-profile individuals

Nice to Have

• Experience supporting talent, entertainers, or public figures
• Background coordinating travel across multiple time zones
• Familiarity with travel apps, airline systems, and itinerary management tools

How to Apply

Please include:

1. Your updated resume
2. A short 1–2 minute Loom video introducing yourself and describing your experience booking travel and managing complex calendars

Only candidates who submit a Loom video will be considered.

If you’re detail-obsessed, dependable, and able to manage travel logistics without missing a beat, this role gives you the chance to support a high-profile entertainer and run the system that keeps their world moving.

Application Process Overview

Our comprehensive selection process ensures we find the right fit for both you and our clients:

1. Initial Application - Submit your application and complete our prequalifying questions
2. Video Introduction - Record an video introduction to showcase your communication skills and work experience
3. Role-Specific Assessment - Complete a homework assignment tailored to the position (if applicable)
4. Recruitment Interview - Initial screening with our talent team
5. Executive Interview - Meet with senior leadership to discuss role alignment
6. Client Interview - Final interview with the client team you'd be supporting
7. Background & Reference Check - Professional reference verification
8. Job Offer - Successful candidates receive a formal offer to join the team

Each stage is designed to evaluate your fit for the role while giving you insights into our company culture and expectations. We'll keep you informed throughout the process and provide feedback at each step.