Executive Assistant / Operations Assistant

I am looking for an exceptional Executive Assistant to support me across both my businesses and personal life.

This is not a traditional virtual assistant role where you will simply be given a checklist of repetitive tasks. I am looking for someone who can become a trusted extension of me — someone who is thoughtful, highly organized, resourceful, comfortable using AI, and able to take ownership of tasks from beginning to end.

I own and operate multiple learning centers in the United States that keep me very busy. My days move quickly, and I need someone who can help bring structure, follow-through, and can communicate very well across many different areas.

The right person will be trusted with sensitive information and will often communicate directly with parents, employees, vendors, and other stakeholders on my behalf. Judgment, discretion, and written communication are therefore extremely important.

What You Will Help With
1. Executive & Personal Support
Manage and organize my calendar
Schedule appointments, meetings, travel, and personal bookings
Research options and make thoughtful recommendations
Complete forms and administrative paperwork accurately
Track deadlines, follow-ups, renewals, appointments, and important dates
Help manage personal projects and miscellaneous tasks
Maintain organized records and documentation
Follow up with people so things do not fall through the cracks

2. Inbox & Communication Management
Help manage a high-volume email inbox
Identify what is urgent, what needs my attention, and what can be handled independently
Draft thoughtful email s in my voice
Respond to routine email s on my behalf once trained
Follow up with parents, employees, vendors, leads, and partners
Maintain a professional, warm, and thoughtful tone in every interaction
Ensure important conversations receive timely follow-up

3. Learning Center / Business Operations
You will support several learning centers and may help with:

Parent communication and follow-ups
Enrollment and lead follow-up
Scheduling and appointment coordination
Vendor communication
Staff scheduling and administrative follow-ups
Tracking operational tasks across multiple locations
Updating spreadsheets, documents, and internal trackers
Preparing reports and organizing information
Following up on invoices, payments, contracts, and paperwork
Helping organize marketing initiatives and community outreach
Maintaining confidential student, family, employee, and business information
Identifying problems before they become bigger problems

You do not need previous learning center experience. I care much more about how quickly you learn, how carefully you work, and how much ownership you take.

What I Am Looking For

You will likely be a great fit if you are:

Extremely detail-oriented: you notice names, dates, numbers, attachments, deadlines, and inconsistencies
An excellent written communicator: your English should be polished, natural, warm, and professional
A problem solver: when something is unclear, you investigate and propose a solution rather than immediately asking what to do
Highly trustworthy and discreet: you will have access to sensitive personal and business information
AI-forward: you actively use tools such as ChatGPT or similar AI platforms to research, draft, organize, summarize, and work more efficiently
Organized: you can manage many small moving pieces without losing track of them
Proactive: you follow up without being reminded
Comfortable with ambiguity: not every task will come with perfect instructions
Calm under pressure: you can handle an upset customer or an urgent request thoughtfully
Able to learn someone else's voice: eventually, an email written by you should sound like it came from me
Comfortable owning mistakes: if something goes wrong, I expect transparency and a proposed solution rather than excuses

Experience with some of these is helpful:

• Gmail
• Google Calendar
• Google Drive / Google Docs / Google Sheets
• ChatGPT and other AI tools
• Canva

Specific software can be taught. Strong judgment and attention to detail are much harder to teach.

Schedule: This position will begin at approximately 4 hours per day, Monday through Friday.

You must be willing to work hours that provide meaningful overlap with the US Eastern Time Zone.

For the right person, this role can become full-time after approximately three months.

I am looking for someone who wants to grow into a long-term role rather than simply pick up a few freelance hours.

Compensation: Compensation will be based on experience and demonstrated capability.

There will be an opportunity for increased responsibility, hours, and compensation for someone who consistently performs at a high level.

IMPORTANT: How to Apply

I receive many applications, so please do not send a generic cover letter.

Instead, include the following in your application:

Task 1 — Email Judgment

A parent email s:

“I’ve called your center twice and nobody got back to me. We came in for an assessment three weeks ago and were promised a call that evening. This feels extremely unprofessional.”

Draft the response you would send on my behalf.

Keep it under 200 words.

Task 2 — Problem Solving

Imagine I send you this message:

“I need to take my mother to a doctor next Thursday afternoon. Find me three well-reviewed options within 20 minutes of my home, check whether they take her insurance, determine their earliest appointment availability, and put everything in a format where I can quickly choose.”

In 5–8 bullet points, explain exactly how you would approach this task from beginning to end.

Do not simply say, “I would research doctors.”

I want to understand how you think.

Task 3 — Attention to Detail

At the very top of your application, write:

Math + Judgment + Ownership

Applications that do not include this line will not be considered.

Task 4 — AI

Tell me:

Which AI tools you currently use
One specific example of how AI has saved you time or improved your work
One situation where you would NOT trust AI's answer without independently verifying it

Task 5 — Your Work Style - Answer these briefly:

What type of manager brings out your best work?
Tell me about a time you caught a mistake before it became a bigger problem.
Tell me about a situation where you were given an unclear task and figured out what to do.
Are you comfortable working with confidential business and personal information?
What hours can you consistently work in US Eastern Time?

Please keep your entire application concise. Being able to communicate clearly without writing unnecessary paragraphs is part of the evaluation.

One Final Note

I care deeply about how people are treated.

Many of the people you will communicate with are parents trusting us with their children, employees relying on us for clear communication, or people with whom I have long-standing professional relationships.

Being fast is important.

Being accurate is important.

But being thoughtful, kind, and exercising good judgment is equally important.

If you are someone who takes pride in doing things exceptionally well, enjoys solving problems, and wants to become an indispensable part of a growing operation, I would love to hear from you.