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

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Rockstar Personal Assistant