Rockstar Personal Assistant
Location: Puerto Rico (full relocation required)
Reports to: CEO
Type: Full-time, highly flexible hours
About the Role
We’re hiring a Rockstar Assistant to serve as Chief of Staff for our Founder / CEO’s (hereafter “Exec”) personal life.
This is not a traditional assistant role. Your job is to keep Exec in his zone—laser-focused on trading—while you handle everything around him, from vitamins and travel to email and project updates.
Key Responsibilities
Day-to-Day Energy & Focus Management
- Stay by Exec’s side, quietly observing and stepping in at the right time.
- Create and maintain checklists for daily routines and ensure Exec follows them.
- Stay on top of Exec’s to do list, knowing what he should be doing and redirecting him towards that whenever he takes a break from trading
- Notice when Exec is distracted or fatigued and redirect him to high-value tasks, rest, or energy-building activities.
- Capture tasks or instructions Exec gives verbally and ensure they’re clearly communicated to the right people.
Health & Wellness Oversight
- Ensure supplements, vitamins, and other essentials are stocked and ready at the right times and that he remembers to take them.
- Coordinate doctor appointments, lab work, and remote health consultations.
- Source and manage personal trainers and other wellness professionals who can flex around Exec’s schedule.
Leadership & Operations
- Oversee Exec’s household and personal operations (chef, cleaners, assistants).
- Delegate execution tasks and ensure completion.
- Monitor and manage Exec’s email inbox, drafting and sending messages on his behalf.
- Ensure Exec’s personal environment (home, office) is distraction-free and well-equipped.
- Manage travel end-to-end: flights, packing, airport transitions, private travel coordination, ensuring a seamless experience.
- Anticipate upcoming needs and resolve problems before they reach Exec.
Social & Lifestyle Management
- Anticipate and proactively manage social dinners, including identifying and inviting Exec’s preferred guests.
- Coordinate with the chef to ensure meals, events, and gatherings align with Exec’s preferences.
- Manage personal correspondence.
What Success Looks Like
- Exec’s personal life runs on rails—healthy routines, smooth logistics, and no loose ends.
- His email and communications are consistently clear, timely, and well-managed.
- You are Exec’s “second brain,” keeping track of open loops, deadlines, and priorities.
Ideal Background & Experience
- Previous experience as a Chief of Staff, Executive Assistant, or operations manager for a high-performing entrepreneur or executive.
- Strong background in managing complex schedules, logistics, and people.
- Proven ability to run communications on behalf of a principal (email, vendors, team).
- Track record of anticipating needs and ensuring follow-through without constant oversight.
- Comfortable in high-intensity, rapidly changing environments.
- Discreet, trustworthy, and confident in handling sensitive information.
- Spanish fluency (written / spoken) required
Qualities We’re Looking For
- Proactive: You don’t just wait for instructions—you act.
- Intuitive: You can read situations, moods, and energy, and respond accordingly.
- Organized: Systems, checklists, and structure are second nature to you.
- Leadership-minded: You orchestrate tasks and people, not just check boxes.
- Discreet: You operate quietly in the background, with complete confidentiality.
- Adaptable: Comfortable switching between personal errands, company coordination, and high-level communications.
Compensation & Perks
- Competitive salary, commensurate with experience.
- Travel opportunities alongside Exec.
- Michelin Star quality private chef meals
Job Type: Full-time
Pay: $130,000.00 - $150,000.00 per year
Benefits:
- Dental insurance
- Flexible schedule
- Health insurance
- Paid time off
- Relocation assistance
- Vision insurance
Work Location: In person
