Personal Assistant To CEO

September 25, 2026

Other Jobs To Apply

Executive Assistant / Life Manager

Location: Miami, FL preferred (hybrid or remote outside of the USA)

Type: Full-time, 1099 contractor

Compensation: $50,000–$70,000/year, based on experience

Hours: 9–5 EST, with availability outside of them for urgent things

Reports to: The founder

About the role

We are a marketing agency run by a founder who moves fast and has a lot going on. He is looking for his first Executive Assistant / Life Manager — someone who takes both the business admin and the personal logistics off his plate entirely.

There is no system in place today. You are not inheriting someone else's process; you're building one and then running it so well that he stops thinking about logistics altogether. He does not want to micromanage — he wants to hand something over and see it done.

What you'll own

Travel: booking flights, hotels and full itineraries.
Calendar & scheduling: managing his calendar end to end and keeping him ahead of what's coming.
Inbox & communication: triaging email, surfacing what matters, handling the rest.
Meeting prep: agendas, briefing notes and follow-ups so nothing gets lost between calls.
Project tracking: he runs many projects at once — you keep the list, the deadlines and the follow-ups straight.
Expenses & finance admin: expense reports, reimbursements, and regular communication with his accountant.
Personal & household: appointments, medical scheduling, personal orders and shopping, groceries, and coordinating cleaners, maintenance and vendors.
Ad hoc support for a small team of three when it's reasonable.

Requirements

Who you are

3+ years as an executive assistant, personal assistant or in a comparable service-driven role. Exceptional candidates with less experience and clear evidence of ownership will be considered.
US-based. Miami preferred, with the ability to be on site around two days a week.
Deeply organised and detail-obsessed — you track everything and nothing falls through the cracks.
Resourceful above all. Given a goal, you figure out the how. You try first and ask second; you don't need to be walked through every task.
Proactive — you handle things before you're asked.
Independent. You'll get autonomy and be judged on results, not hours logged.
Calm and easy to work with; plans change often.
Discreet and trustworthy — you'll have access to personal and financial information.
Comfortable with technology and quick to learn new tools; the business runs on Airtable and GoHighLevel.
Excellent written and spoken English.

Nice to have

Project management or operations experience.
Experience in or around a marketing/creative agency.
Experience supporting a founder directly

Benefits

What's on offer

Direct, close working relationship with a founder who gives real autonomy and real trust.
A role you get to design — you're building the system, not maintaining someone else's.
Genuine variety: business admin one hour, personal logistics the next.
Flexible, low-bureaucracy environment — time off is handled by conversation, not policy.

Skills:
Accounting, Business Administration, Calendar Management, English Language, Executive Assistant Skills , Expense Reports, Financial Administration, Logistics, Marketing, Organizational Skills, Presentation/Verbal Skills, Project Tracking, Project/Program Management, Reimbursement, Time Management, Writing Skills

Trivium

Back to blog

Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...