Remote Executive Assistant job (M/F) in Puerto Rico
Job description
A private principal based in Puerto Rico is seeking a full-time Remote Executive Assistant for hands-on personal support.
This is a unique execution-focused role conducted entirely in writing, with no phone or video calls at any stage.
The assistant will work directly with the Principal via Telegram during Atlantic Standard Time hours, managing personal errands, appointments, paperwork, vendor coordination, and follow-through on all tasks.
The role requires someone who can navigate situations where the default is to call or meet in person, and find written solutions instead. All communication is brief, clear, and written, with daily end-of-day reports.
The position offers the flexibility of remote work from any location, provided the candidate maintains AST business hours and adheres to strict written communication protocols.
Responsibilities
- Source and order personal items, including hard-to-find products in Puerto Rico and arrange US shipments to the island
- Schedule and confirm in-home appointments, services and reservations with written instructions provided in advance
- Complete personal paperwork, forms and applications, liaising with agencies, consulates and banks in writing
- Prepare documents for e-signature and coordinate mobile notary appointments
- Collect written quotes from vendors, research options and present clear recommendations
- Follow up persistently with vendors, service providers and deliveries until each task reaches completion
- Provide daily end-of-day written reports covering completed tasks, work in progress, blockers and items requiring Principal input
- Set up all vendors and providers to communicate in writing from first contact
- Maintain prompt written responses during working hours via Telegram
- Manage all communication in short, scannable messages with one message per matter
Requirements
- 3 to 5 years of executive or personal assistant experience, preferably supporting a private individual remotely
- Exceptional problem solver who finds workarounds rather than accepting initial obstacles, particularly where a phone call or in-person visit would normally be expected
- Sound judgment, anticipating downstream consequences before acting
- Asks precise questions when clarification is needed rather than guessing
- Honest about limitations and reports obstacles with alternative solutions
- Excellent written English, with the ability to communicate clearly and concisely
- Completely comfortable working without phone or video calls, conducting all business through written channels such as Telegram
- Works quickly with minimal ramp-up time
- Handles confidential information with absolute discretion
- Proficient with Telegram, email, Proton, e-signature platforms, shared documents and AI tools
- Experience with government agencies, consulates or banks is an advantage
- Spanish language skills are a plus but not required
Work conditions
- Full-time remote position, Monday to Friday during Atlantic Standard Time (AST) hours, with some schedule flexibility required
- Candidates can be based anywhere, provided they reliably maintain AST working hours
- Reports directly to the Principal and the Executive Chief of Staff: tasks come from the Principal, while the Chief of Staff handles onboarding, payments and administrative matters
- Conducted entirely in writing via Telegram, with absolutely no phone or video calls at any stage, including interviews and daily work
- Selection process:
- Written application including problem-solving examples
- Written interview conducted by message
- Paid trial period working on real tasks
- Background check and signed NDA before access to personal information
- The Principal's identity is disclosed only after the NDA is signed
- Strict confidentiality and written communication protocols are non-negotiable
- A great position for someone who has mastered the art of logistics
Salary
My name is Tiffany Kolosick, and I have been working in the private service industry for more than 20 years. Before transitioning into recruiting, I held nearly every role within a private household, giving me firsthand insight into the responsibilities, expectations, and challenges faced by both clients and household professionals. This experience allows me to view each placement through the unique lens of both the client and the candidate. My primary goal is to create successful, long-term placements by ensuring that the needs, expectations, personality, and working styles of both parties are aligned. In my experience, when a placement is truly a win for both the client and the candidate, it creates the foundation for a successful and lasting relationship.
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