KS1087 - Full-Time Executive Assistant - Fully Remote

Overview

A principal living in Puerto Rico is seeking a full-time Executive Assistant to work 100% remotely.  You will work directly with the principal on personal tasks and with his chief of staff, and all communication will be in writing.  The candidate can live anywhere as long as they are comfortable working in the Atlantic Standard Time zone.  The schedule is Monday through Friday.  The whole process is conducted in writing.  There will be a written application: CV plus short written answers describing problems the candidate has solved remotely.  This will be followed by a written interview: a live exchange by message.  Paid trial: shortlisted candidates work in parallel on the same real tasks. We assess process, judgment, and the quality of written updates, not only outcomes.  Finally, a background check and NDA are completed before any access to personal information or the principal's identity is revealed. The principal is ready to hire immediately.    

Responsibilities

• All communication is in writing, mainly by using an app called Telegram.  No phone or video calls are used at any stage, including interviews, onboarding, and day-to-day work. This is a firm requirement of the role.
• Keep messages short and easy to scan. The Principal prefers brief updates to long explanations.
• Send one message per matter, stating where it stands and exactly what is needed from the Principal, if anything.
• Respond promptly in writing during working hours.
• This is a hands-on execution role, not an inbox-and-calendar role.
• Many tasks involve places where the usual answer is “come in person” or “call us,” and the assistant finds the way to get them done in writing.
• Personal errands and purchases: sourcing and ordering items, including hard-to-find items in Puerto Rico, and getting US purchases shipped to the island.
• Appointments and bookings: scheduling and confirming in-home appointments, services, and reservations, with written instructions sent in advance.
• Personal paperwork: completing forms and applications, and working with agencies, consulates, and banks on the Principal's personal documents.
• Signatures: preparing documents for e-signature and booking mobile notaries.
• Quotes and research: collecting comparable written quotes and presenting options with a clear recommendation.
• Follow-through: chasing vendors, deliveries, and replies until each task is closed.
• Daily end-of-day report: a short written update every workday covering what was completed, what is in progress, what is blocked, and what is needed from the Principal.

Requirements

• 3 to 5 years as an executive or personal assistant, ideally supporting a private individual.
• A track record of getting things done remotely, with examples that can be described in writing.
• Experience dealing with government agencies, consulates, or banks is a plus.
• Comfortable with Telegram, Proton, e-signature platforms, and shared documents, and works securely by habit.
• A problem solver. Finds the workaround instead of accepting the first “no.”
• Sound judgment. Spots the downstream consequences of a task before acting and raises them with the right person.
• Asks well. When something is unclear, asks one precise question. Does not guess or go quiet.
• Honest about dead ends. Reports what can't be done, why, and the alternatives. Never implies progress that hasn't happened.
• Absolute discretion. Initiative is welcome. If unsure whether something is theirs to handle, asks first.
• Fast. Contributes from the first week without a long ramp-up.
• Excellent written English. Clear and concise.
• Spanish is a plus, not a requirement.

Salary and Benefits

The client is offering $ 130- 150 K, depending on experience.  This is a 1099 independent contractor role.