Executive Assistant & Founder Support VA - Full-Time

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TYPE OF WORK

Full Time

SALARY

$500/month to start, review at 90 days

HOURS PER WEEK

40

DATE UPDATED

Aug 18, 2026

JOB OVERVIEW

THIS IS NOT A BASIC "DO WHATEVER I SEND YOU" VA JOB.

The $2 Bill Brand helps entrepreneurs, coaches, consultants, and experts become the recognized authority in their industry. Our founder, Brad Holcman, is building a business around a simple but powerful idea:

Do not be the best. Be the ONLY.

Brad has a lot of ideas, opportunities, commitments, projects, and responsibilities moving at once. He needs someone who is naturally organized and genuinely enjoys turning a messy stream of tasks, voice notes, meetings, and reminders into a calm, visible plan.

You will work directly with Brad as his Executive Assistant and Founder Support VA. Your job is to help make sure important business and personal commitments do not disappear, priorities are clear, follow-ups happen, the calendar supports what matters, and Brad knows what deserves his attention today.

This is a full-time, long-term role for someone who is hungry to learn, takes ownership, communicates clearly, and wants to become an indispensable right hand over time.

THE BASICS
Type of work: Full time, 40 hours per week
Pay: $500 USD per month
Start date: As soon as the right person is found
Location: Philippines
English level: Fluent / Advanced
Experience level: Intermediate to Advanced
Schedule: Full-time remote. Required weekday overlap of 9:00 a.m. to 12:00 p.m. U.S. Eastern Time. Remaining hours are flexible around agreed deliverables.

WHAT YOU WILL DO

1. Run the founder's daily operating system
You will collect tasks and ideas from messages, meetings, voice notes, email, and conversations. You will put them into one organized task system, clarify deadlines and next actions, and keep a close eye on what is due, stuck, or forgotten.

Each workday, you will prepare a short founder brief with the day's highest priorities, calendar, deadlines, follow-ups, and decisions needed. At the end of the day, you will close loops and prepare the next day so nothing important is lost.

2. Protect the calendar and inbox
You will help organize Brad's Google Calendar, schedule and reschedule meetings, add preparation details, protect focused work time, avoid conflicts, and make sure important meetings have the right information attached.

You will help organize email and messages under agreed rules. You will flag urgent items, draft simple replies when appropriate, track waiting-on responses, and make sure people are not left without an answer. You will never send sensitive communications or make commitments without clear approval rules.

3. Keep business projects and follow-ups moving
You will track important priorities across our content, marketing, coaching, client, and team work. You will follow up with people, maintain simple status views, convert meeting notes into next actions, and alert Brad early when something needs a decision or is at risk of slipping.

You are not expected to do every specialized job in the company. Your responsibility is to make sure requests, deadlines, and decisions do not get lost.

4. Support approved personal logistics
With clear privacy boundaries, you may help research and coordinate personal appointments, travel options, family-calendar reminders, gifting, reservations, orders and returns, and other practical logistics that protect Brad's time. You will always ask before making purchases, sharing sensitive information, or doing anything outside pre-approved rules.

WHAT SUCCESS LOOKS LIKE
First 30 days: You create one clean task/follow-up system, learn Brad's preferences, establish the daily brief, improve calendar habits, and begin reliably capturing actions from meetings and messages.

Days 31-60: You run a consistent weekly priority review, keep a forward-looking calendar view, track key projects, and proactively close routine communication loops.

Days 61-90: Brad trusts the system. He knows his priorities, important commitments are anticipated, and business and personal logistics are more organized with fewer reminders coming from him.

WHO WILL DO WELL HERE
You have at least one year of meaningful administrative, executive-support, operations-support, or project-coordination experience. You may have supported a founder, manager, small business owner, agency owner, or executive.

You do not need to have been a Chief of Staff. But you must be able to explain the system you personally used to stay organized.

You have excellent written and spoken English. You are highly reliable, calm under pressure, discreet, detail-oriented, comfortable using Google Workspace, and not afraid to ask a clear question when the next step is ambiguous.

Experience with Google Calendar, Gmail, Google Drive, ClickUp, Asana, Notion, Trello, Slack, WhatsApp, Zoom, travel research, and AI productivity tools is helpful. Strong judgment, follow-through, and communication matter more than knowing every tool.

SKILLS THAT MATTER FOR THIS ROLE
Executive assistance, administrative support, calendar management, email management, task management, project coordination, personal assistance, Google Workspace, Google Calendar, Gmail, meeting management, online research, documentation, written English, problem solving, ClickUp, Asana, Notion, travel planning, AI productivity tools.

THIS ROLE IS NOT A FIT IF
Do not apply if you want a passive role where you simply wait for a written list of tasks. Do not apply if you cannot reliably work the required Eastern-Time overlap, have unstable internet without a backup plan, or are uncomfortable handling confidential business and personal information with maturity.

We are not looking for someone to be on call 24/7, perform every specialized function in the company, or make financial or personal decisions without approval. We are looking for a proactive, reliable assistant who wants to grow into a true right-hand support role.

HOW TO APPLY
Start your application with this exact phrase:

I am the Operating System.

Applications without that phrase will not be considered.

Please include ALL of the following:

1. Your resume or OnlineJobs profile and a short explanation of whom you supported in your most relevant role.

2. A two-minute Loom or video introduction. Tell us about the messiest workload you had to organize and the system you used.

3. In 250 words or fewer, answer this question: A founder sends scattered voice notes, three meeting requests, two personal reminders, and five urgent-looking emails. What do you do first, and what does your end-of-day update look like?

4. A redacted example of a tracker, agenda, calendar-preparation template, daily plan, or follow-up system you created. Never share confidential prior-employer information.

5. Your availability in Philippines Time, confirmation of the Eastern-Time overlap, internet backup plan, and expected monthly pay.

Shortlisted candidates will complete a paid US$20 practical exercise involving a fictional task dump and calendar. We will evaluate how you prioritize, ask questions, organize follow-ups, and communicate, not how fancy your design is.

WHY JOIN US
You will work directly with a founder who cares about growth, creativity, and building something that stands out. This is an opportunity to become a trusted part of a small, ambitious business and grow in responsibility as you prove yourself.

SKILL REQUIREMENT
Personal Assistant Administrative Support Executive Assistance
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