We're looking for a Executive Assistant to support a founder and their family across personal administration, scheduling, household coordination, and eventually business operations. This role starts on the personal side and grows into business support as trust is established.
The founder runs a fast-moving operation and has documented systems for most recurring tasks including travel preferences, ordering habits, decision-making processes, and family logistics. Your job is to access those systems, execute from them, and proactively take things off the plate without being asked twice. This is not a role for someone who waits for instructions. The ideal hire is confident stating what they need, takes full ownership of their tasks, and knows how to use AI tools including Claude Cowork as a real part of how they work. If you are proactive, organized, discreet, and comfortable scaling from personal logistics into business support over time, this role is a strong fit.
Why You'll Want to Join
- You will be paid in USD (bi-monthly: every 15th and 30th)
- Paid Time Off in accordance with company policy
- Observance of Holidays per company guidelines
- 100% remote setup so you can work wherever you're most productive
- This role requires availability during US Pacific Time business hours
- Start with a clearly scoped personal and family support role with a defined path to grow into business operations support
- High-trust, high-ownership role with direct access to the founder and real room to expand as you demonstrate judgment
What You'll Work On
Scheduling and Appointment Management
- Make outbound calls during business hours to schedule appointments for the founder, family members, and household contacts
- Coordinate across multiple calendars including the founder, partner, childcare, and family schedules to keep everything synced
- Set up medical, personal, and professional appointments and ensure all logistics are confirmed and communicated
- Manage scheduling conflicts proactively and keep everyone informed without requiring follow-up
Household and Family Coordination
- Coordinate with household staff including nanny scheduling and communication
- Handle recurring household logistics such as meal ordering, household supply management, and vendor coordination using documented preferences and systems
- Support family event logistics including social dinners, community events, and gatherings
- Assist with baby and family-related administrative tasks as needed
System Access and Documentation
- Access and operate within established systems and shared documentation to execute tasks consistently with documented preferences
- Use existing decision-making frameworks and preference logs rather than asking repeated clarifying questions
- Help maintain and improve documentation so the systems stay current as preferences evolve
- Leverage Claude Cowork and other AI tools to work faster and more accurately across all tasks
AI-Assisted Workflow
- Use Claude Cowork daily as a core part of how tasks are planned and executed
- Apply AI tools to automate or streamline recurring administrative tasks
- Support the founder in teaching and refining how AI tools are used across their personal and business operations
Business Operations Support (Growth Path)
- As trust is established, take on increasing responsibility on the business side of operations
- Support the founder with business scheduling, communications, project coordination, and other executive support tasks
- Function increasingly as a business partner or chief of staff adjacent resource over time
What You Bring
- Proven experience as a personal assistant, family EA, household manager, or similar role supporting a high-trust principal
- Genuinely proactive — comfortable taking ownership of tasks, stating what you need, and moving without waiting for detailed direction
- Comfortable making outbound calls during US business hours to schedule appointments and coordinate logistics on behalf of others
- Familiarity with Claude Cowork or strong willingness and aptitude to learn it quickly — AI fluency is expected for this role
- Excellent written and verbal English communication skills
- Discreet, reliable, and highly organized with strong attention to detail across scheduling, documentation, and coordination tasks
- Comfortable working within established systems and documented preferences rather than building from scratch
- Available during US Pacific Time business hours
Nice to Have
- Experience supporting both personal and business operations for a founder or executive
- Familiarity 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
- Prior experience scaling from personal EA into business operations or chief of staff adjacent work
How to Apply
Please include:
- Your updated resume
- A short Loom video (1 to 2 minutes) 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.
If you are proactive, discreet, comfortable with AI tools, and want a high-trust role that starts on the personal side and grows into real business partnership, this role gives you the foundation and the path to do your best work.
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.
