Executive & Personal Assistant (U.S. Eastern Time)

Short-Term Rental Company | Highly Organized | Direct Support to the Owner

We are seeking a high-performing Executive & Personal Assistant who will work directly under the owner to organize, streamline, and elevate both business operations and personal life. Our short-term rental business already has dedicated staff, established workflows, and a large library of SOPs — but the owner needs someone who can bring everything together and make life run smoothly.

*** Starting Salary is $550 USD. Salary increase will strictly depend on performance and output.

*** Experience with pricelabs is a PLUS
*** This is mainly an Admin position to tackle various task, so you must be quick

Company Size - 80 Units

This role requires someone who can take initiative, build structure from scratch when needed, and genuinely WOW the owner with exceptional organization, communication, and systems thinking. To be hired — and to keep this role — your performance must stand out immediately and consistently.

What You’ll Do

Business / Executive Support

- Work directly under the owner, assisting with daily work tasks, workflow oversight, and follow-ups.
- Organize and manage the owner’s work calendar: appointments, meetings, deadlines, reminders.
- Prioritize tasks and ensure essential follow-ups happen without the owner having to ask.
- Assist with short-term rental guest communication if needed.
- Organize digital files, SOPs, spreadsheets, operational documents, and internal systems.
- Manage recurring business tasks (renewals, subscriptions, app settings, listing updates).
- Perform administrative tasks using the company’s apps, software, and tools.
- Review current workflows and build improved systems for:
- Task management
- Daily and weekly reporting
-Dashboard views
- Operational oversight
-Owner summaries
- Act as the owner’s voice for minor decisions when unavailable.
- Learn the company operations well enough to cover shifts temporarily if staff members call out.
- Work on special projects, research tasks, and one-off requests.

Training Provided

You will receive full training for all business-related responsibilities.
We have extensive SOPs, documentation, and step-by-step processes to support you in learning the operations. If you are organized and tech-savvy, you will learn everything quickly.

Personal Life Support (Remote, Non-Physical)

- Book travel, flights, hotels, reservations, itineraries.
- Handle online errands: research, price comparisons, online orders, returns.
- Track personal bills, memberships, renewals, subscriptions, and follow-up items.
- Research kids’ classes, activities, local services, providers, pricing, and ratings.
- Prepare and organize personal reminders, deadlines, and schedules.
- Keep the owner organized in all areas of life — even when things get hectic.

What You MUST Bring

- Exceptional organizational skills — the kind that truly impresses and WOWs.
- Ability to create structure even when there is no template or clear direction.
- Independent thinker who produces polished results with minimal supervision.
- Strong problem-solving and analytical skills.
- Ability to turn messy or unclear processes into simple, clean systems.
- Proactive — you anticipate needs before the owner even mentions them.
- High attention to detail and accuracy.
- Ability to prioritize, multitask, and meet deadlines in a fast-paced environment.
- Fluent English (spoken and written).
- Highly tech-savvy and fast learner with new software.
- Reliable and responsive during U.S. Eastern Time hours.
- Comfortable handling both business and personal tasks with discretion.
- Resourceful, proactive, and solution-oriented.

Nice-to-Haves

- Experience in short-term rentals (Airbnb, VRBO).
- Previous Executive Assistant or Personal Assistant experience.
- Experience using task or project management tools.
- Bookkeeping experience is a strong plus.

What Will WOW the Owner

- You can analyze the owner’s habits, tasks, and systems and present better ways to manage everything.
- You create order, clarity, and structure without needing to be told what to do.
- You propose new systems, dashboards, or workflows that simplify the owner’s daily life.
- You ensure nothing falls through the cracks — ever.
- You deliver consistent results with high quality and strong initiative.
- You help unify the business and personal tasks into one easy-to-understand system.

If You Do Not Have Experience…

Please DO NOT apply if you ONLY need a job, if you are not organized and if you are not serious about it. Screening will be very detailed. Please don't waste your time or ours.

How to Apply

Send an email to ----------
with the subject line: "Assistant Extraordinaire"

Please Note:
Include:

- Your resume
- A brief cover letter explaining:
-Any experience assisting executives or handling admin tasks
- Why you’re the perfect fit to manage both owner’s life/work