Executive Assistant (Personal and… at Hire Overseas · San José

💼 Executive Assistant (Personal and Business) 🌍 Open to Latin America: This role is open to candidates based in Latin America. 🏠 Remote

About Our Client

Our client is a busy founder who needs dependable support across personal administration, scheduling, household coordination, and family logistics. They've documented their systems for recurring tasks, including travel preferences, ordering habits, and decision-making processes, so the right hire can execute with confidence from day one.

About the Role

We're looking for a Personal Executive Assistant to support a founder and their family across personal administration, scheduling, household coordination, family logistics, and social events. The role is primarily personal: the starting point is appointment making, and everything else builds from there as trust is established.

You'll access a shared brain of documented preferences and systems daily and execute from it. This is not a role for someone who waits to be told what to do. The ideal hire is proactive, confident stating their own needs and preferences, takes full ownership of tasks end to end, and uses AI tools, including Claude Cowork, as a real part of how they work.

Responsibilities

• Make outbound calls during business hours to schedule and coordinate appointments, the starting point and core of the role
• Set up medical, personal, and professional appointments for the founder and their family
• Sync across multiple calendars, including the founder, partner, and childcare, and manage conflicts proactively
• Coordinate with the nanny on scheduling and logistics
• Use the shared brain daily to execute tasks from documented preferences and systems rather than asking repeated clarifying questions, and help keep it current
• Use Claude Cowork and other AI tools as a core part of planning and executing tasks, and help refine how AI is used across personal and household operations
• Support planning and logistics for hosted dinners and community events
• Manage takeout ordering from documented preferred restaurants and order history, placing orders directly via DoorDash or similar platforms
• Assist with family logistics, including baby-related tasks and family administrative tasks, using established systems

What We're Looking For

• Proven experience as a personal assistant, household manager, or family EA supporting a high-trust principal
• Genuinely proactive, taking ownership of tasks end to end without waiting for detailed direction
• Comfortable stating your own preferences and needs as part of a healthy working relationship
• Confident making outbound calls during US business hours to coordinate appointments and logistics on behalf of others
• Familiarity with Claude Cowork, or strong willingness and aptitude to learn it quickly, as AI fluency is expected
• Discreet, reliable, and highly organized with strong attention to detail
• Comfortable working within documented systems and preferences rather than building from scratch

Nice to Have

• Experience with Claude Cowork or similar AI workflow tools
• Background coordinating household staff, childcare logistics, or family scheduling
• Experience supporting social event planning or community hosting
• Familiarity with managing shared documentation systems or knowledge bases

Work Schedule

• 100% remote setup so you can work wherever you're most productive
• This position operates on a full-time basis, with dedicated hours to ensure alignment with the team and delivery of quality work
• Availability during US Pacific Time business hours

Compensation & Time Off

• Compensation paid in USD
• Paid bi-monthly on the 15th and 30th
• Paid Time Off according to company policy
• Holidays observed according to company guidelines

Application Requirements

Please submit:

• An updated resume
• A 1–2 minute Loom video introducing yourself, describing your experience supporting a principal across personal and household logistics, and explaining how you use AI tools as part of your daily workflow

Only candidates who submit a Loom video will be moved to the next step of the hiring process.

Application Process Overview

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

Initial Application - Submit your application and complete our prequalifying questions

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