We are seeking an exceptionally resourceful Executive Assistant to increase the effectiveness of a fast-moving entrepreneur and CEO.
This is not a traditional administrative role focused only on scheduling meetings and completing assigned tasks. It is a high-trust position for someone with excellent judgment, strong follow-through, intellectual curiosity, and a bias toward action.
Your primary objective is to reduce the number of things the CEO must personally manage, remember, research, coordinate, and follow up on.
You will attend selected business and personal meetings, document decisions and action items, personally execute everything you can reasonably own, assign remaining tasks to the appropriate team members, and follow through until every commitment is completed.
Key responsibilities include:
- Attend selected meetings and produce concise notes organized by decisions, action items, owners, and deadlines.
- Personally execute the maximum reasonable number of resulting action items.
- Assign remaining tasks and rigorously track them through completion.
- Manage the CEO’s inbox, draft communications, surface priorities, and maintain an organized follow-up system.
- Produce a concise daily digest containing important updates, decisions needed, deadlines, and unresolved issues.
- Manage the CEO’s calendar, appointments, reminders, and scheduling conflicts.
- Conduct detailed research involving vendors, talent, partners, services, purchases, healthcare providers, and business or personal decisions.
- Compare options and present clear recommendations covering cost, quality, risks, and next steps.
- Coordinate domestic and international travel, including flights, accommodations, transportation, reservations, itineraries, and supporting documentation.
- Coordinate with vendors, obtain estimates, monitor deliverables, and follow up on late or incomplete work.
- Track financial deadlines, receipts, payments, and administrative documentation.
- Coordinate healthcare, dental, fitness, wellness, and personal appointments.
- Convert voice notes, emails, conversations, and ideas into organized tasks with priorities, owners, and deadlines.
- Document recurring procedures and identify opportunities for automation, delegation, and process improvement.
Requirements
- At least three years of experience as an Executive Assistant, Personal Assistant, Administrative Assistant, Project Coordinator, or similar operator.
- Previous experience directly supporting a founder, entrepreneur, or C-level executive is strongly preferred.
- Excellent written and spoken English.
- Exceptional organization and attention to detail.
- Strong judgment and the ability to operate with incomplete information.
- Demonstrated history of proactive problem-solving, taking ownership, and closing loops.
- Ability to communicate complicated information clearly and concisely.
- Comfortable respectfully challenging an instruction when you identify a better approach, missing information, or significant risk.
- High level of integrity, professionalism, discretion, and confidentiality.
- Strong proficiency with Google Workspace, Slack, Zoom, and project-management platforms such as Monday.com, Asana, ClickUp, or Trello.
- Comfortable learning automation tools, AI platforms, and unfamiliar technology.
- Ability to distinguish between tasks you can execute independently and decisions requiring CEO approval.
- Reliable computer, high-speed internet connection, quiet working environment, and backup internet access.
- Availability for a consistent four-hour daily block, Monday through Friday, overlapping with US Eastern Time.
- Full responsiveness and availability during scheduled working hours.
- Willingness to disclose any existing employment or recurring client commitments before hiring.
- No other work may conflict with the agreed working schedule.
- Willingness to complete a paid practical exercise and provide verifiable professional references.
This position is not appropriate for someone who requires detailed instructions for every assignment, regularly needs deadline reminders, identifies problems without proposing solutions, or considers a task finished simply because a message was sent.
Benefits
- USD $850 to $1,000 in monthly compensation, based on experience and demonstrated ability.
- Fully remote
- Direct working relationship with the CEO.
- Meaningful ownership over business and personal operations.
- Exposure to complex business decisions, research, systems, vendors, travel, and executive operations.
- Opportunity to develop skills in automation, AI tools, project management, and operational execution.
- Performance-based compensation reviews.
- Potential to assume greater responsibility and expand into a full-time position.
- Potential to shift to full time.