STR Operations & Executive Assistant (Hospitable, Quo, ClickUp, Claude/Perplexity)

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: TYPE OF WORK

Part Time

: SALARY

500–$750

: HOURS PER WEEK

TBD

: DATE UPDATED

Apr 2, 2026

JOB OVERVIEW

Short-Term Rental Operations & Executive Assistant (Hospitable, ET Hours)

About us
We are a growing short-term rental business with 4 active listings managed through Hospitable. We consistently book most weekends and are building a streamlined, systems-driven operation. I'm a busy physician/owner and am looking for a long-term partner who can help run day-to-day STR operations and also support me as a professional assistant as the business grows.

Role overview
You will start as a Short-Term Rental Operations & Executive Assistant, with a clear path to grow into an Operations Lead role as we add more properties and complexity. This is an hourly, remote, independent-contractor position with required overlap in US Eastern Time and consistent weekend coverage.

Key outcomes (first 60–90 days)
- Guest messages are answered within agreed response times during your coverage window, in a warm, professional, hospitality-focused tone.
- Hospitable inbox and calendars are clean and accurate (no double bookings, correct rules, templates kept up to date).
- Cleaners and turnovers are coordinated smoothly, with minimal surprises for guests or vendors.
- Bookkeeper receives organized statements, invoices, receipts uploaded to Google Drive weekly.
- My personal schedule and STR-related admin are more organized and predictable because of your support.

Core responsibilities

Short-term rental operations
- Manage guest communication across Airbnb/OTAs using Hospitable (pre-stay questions, check-in issues, mid-stay questions, check-out, reviews when needed).
- Follow and improve existing messaging templates; document new edge cases and solutions as SOPs.
- Monitor reservations, calendar changes, special requests, and potential issues, and escalate to me only when needed.
- Coordinate turnovers: schedule and confirm cleaners, share guest details and special notes, follow up for photos, and flag issues (damage, missing items, supply restocking).
- Track basic property issues/maintenance requests and help arrange vendors when requested.

Bookkeeper coordination & admin
- Collect and upload STR statements, invoices, receipts, payouts to organized Google Drive folders weekly.
- Coordinate with bookkeeper: flag unusual charges, provide missing documents, answer basic questions.
- Maintain organized digital records (receipts, invoices, vendor info, warranties, etc.) in Google Drive.
- Prepare simple weekly summary reports of bookings, payouts, and expenses for bookkeeper review.

Executive assistant support
- Help manage my calendar for STR-related calls, vendor meetings, and important deadlines.
- Assist with inbox triage (tagging/organizing STR-related emails, flagging items that need my attention).
- Conduct research and present concise options (e.g., cleaners, vendors, furnishing or supplies, local services).
- Support small personal/administrative tasks as agreed (e.g., simple travel research, document organization).

Tools you'll use
- Hospitable (PMS)
- Airbnb/other OTAs as needed
- Quo (business phone system for calls/texts)
- Turnover/cleaning coordination tools (or cleaner communication via WhatsApp/SMS/email)
- ClickUp (task/project management)
- Google Workspace (Docs, Sheets, Drive, Calendar)
- AI productivity tools: Claude.ai, Perplexity.ai (for research, SOP drafting, guest message optimization, vendor analysis)
- Messaging (e.g., Slack/WhatsApp)
- Time-tracking tool (e.g., Clockify/Upwork tracker) for hourly work

Requirements
- Excellent written and spoken English; you must be able to write clear, friendly, professional guest messages and internal updates.
- Prior experience with short-term rentals, hospitality, or guest communication (Airbnb / Vrbo / ---------- / STR-focused VA work strongly preferred).
- Comfortable using Hospitable, Quo, ClickUp, Claude.ai, and Perplexity.ai to improve efficiency (guest calls/texts via Quo, task tracking in ClickUp, researching cleaners/vendors via Perplexity, drafting SOPs via Claude, optimizing workflows).
- Strong organizational skills for Google Drive file management and bookkeeper coordination.
- Comfortable using PMS tools (Hospitable experience is a big plus) and learning new software quickly.
- Ability to follow SOPs and also suggest improvements when you see better ways to do things.
- Reliable internet, backup connectivity plan, and a quiet environment for calls when needed.
- Consistent overlap of at least 4 hours per day with US Eastern Time, plus reliable availability during key weekend check-in/check-out windows.

Nice to have
- Direct experience with Hospitable.
- Experience coordinating cleaners/maintenance for STRs.
- Experience organizing financial documents for accountants/bookkeepers.
- Experience supporting a busy professional (EA, PA, or ops assistant role).
- Experience using Quo (business phone), ClickUp, Claude.ai, or Perplexity.ai for operations, calls/texts, task management, research, or guest communication.

Compensation & schedule
- Independent-contractor role, hourly.
- Expected range: USD 10–15 per hour, depending on experience and fit.
- Approx. 20–30 hours per week to start, with the possibility to increase as the business grows and as you take on more responsibility.
- Weekly payment (after submitted and approved timesheet) via agreed method.
- Clear performance-based review at 60 and 90 days, with potential rate increase based on reliability, ownership, and results.

How to apply (read carefully)
To be considered, please follow these steps exactly:

1. Subject line: Use "ET STR Ops & EA – [Your Name]".
2. Loom video (2–3 minutes): Introduce yourself and briefly describe:
- Your STR/VA/EA experience.
- A challenging guest or client situation you handled and how you resolved it.
3. Written answers (in your message):
- Where are you located and what are your typical working hours in your local time?
- What is your internet setup and backup plan?
- Describe your experience with Airbnb/STR operations and any tools like Hospitable, Quo, ClickUp, Claude.ai, Perplexity.ai, etc.
- Give an example of how you stay organized when you're juggling multiple tasks (guests, cleaners, bookkeeper coordination, and admin).
- What experience do you have with Quo (business phone), ClickUp, Claude.ai, or Perplexity.ai? Give 1 specific example.
4. Samples (if you have them):
- One or two anonymized examples of guest messages you've written (before/after a tricky situation), or a brief summary of a process you helped improve.

Only candidates who follow the instructions above will be considered. This is a long-term role with room to grow, and I'm looking for someone who wants to become a trusted partner in the business—not just a short-term task taker.

SKILL REQUIREMENT

Property Management Airbnb Virtual Assistant

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STR Operations & Executive Assistant (Hospitable, Quo, ClickUp, Claude/Perplexity)

Please login or register as jobseeker to apply for this job.

TYPE OF WORK

SALARY

HOURS PER WEEK

DATE UPDATED

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