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TYPE OF WORK
Full Time
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SALARY
1000
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HOURS PER WEEK
56
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DATE UPDATED
Aug 14, 2026
STOP. If you do not have a minimum of 5 years of experience managing a short-term rental portfolio, do not apply. Do not send a message. Do not reach out. This role is not for beginners or those transitioning into STR management.
About the Role
We operate a portfolio of 50 short-term rental units across multiple U.S. markets. We are looking for a seasoned, self-sufficient Virtual Assistant who has done this before — at scale — and knows what it takes to run a high-performing STR operation without hand-holding.
This is not a task-taker role. We need a problem-solver who can think independently, anticipate issues before they escalate, and execute without needing constant direction.
You Must Have:
• 5+ years of hands-on experience managing short-term rental portfolios
• Active experience on Airbnb,
• Experience managing 30+ properties simultaneously
• Proficiency in at least one Property Management System (PMS) — such as Guesty, Hostaway, Lodgify, or similar
• Strong Microsoft Excel / Google Sheets skills for tracking, reporting, and operational organization
• Fluent English — written and spoken — with professional communication ability
• Fast, reliable internet connection (this is non-negotiable)
• Exceptional multitasking and organizational skills — you will be managing guests, owner communications, maintenance coordination, and platform operations simultaneously
What You’ll Actually Be Doing:
• Managing guest communications across all platforms from inquiry to checkout
• Monitoring and responding to reviews — flagging issues, crafting responses
• Coordinating with cleaning teams, maintenance vendors, and local contacts
• Identifying and resolving guest satisfaction issues proactively
• Flagging pricing opportunities, calendar gaps, and listing performance issues
• Escalating only what truly needs escalation — everything else, you handle
Who You Are:
You are organized, fast, and resourceful. You don’t wait to be told what to do — you see a problem and you fix it. You understand that in STR management, your response time and judgment directly affect revenue and reviews. You take ownership.
To Apply:
Do not send a generic application or resume. I will not respond to those.
Instead, send me a direct message with your written answers to the following questions only:
Before we set up a call, would you mind answering these in writing? No need to be formal — short answers are fine.
1. Walk me through your background in property management or hospitality operations. How many units, which markets, and what were you personally responsible for?
2. What software have you worked in day to day? (PMS like Hospitable/Guesty/Hostaway, Airbnb/Booking/VRBO extranets, pricing tools, cleaning tools like Turno, Slack, spreadsheets, anything else.) Which are you strongest in?
3. How comfortable are you learning a new system from scratch — with documentation and a walkthrough, but not hand-holding? Give me a specific example of a tool or process you picked up recently and how long it took you to get fluent.
4. Describe how you plan your day. What does your calendar or task list actually look like, and how do you keep things from slipping when five things break at once?
5. How do you prioritize when a guest issue, a cleaner no-show and a landlord
6. What are your working hours and time zone, and how do you handle after-hours or weekend escalations? Is that something you’ve done before?
7. Are you currently working with other clients or a business of your own? How many hours a week could you realistically commit here?
8. Do you have experience managing vendors — cleaners, handymen, contractors? How do you hold them accountable when quality drops?
9. How would you rate your spoken English, and how much of your past work involved live phone or video calls with guests, property managers or owners? (Feel free to send a 60–90 second voice note answering questions 1 and 4 — that covers this one too.)
10. What does your ideal setup look like — internet speed, backup power/internet, and where you’d be working from?
11. What are your compensation expectations, and how soon could you start?
Once I have these I’ll get a call scheduled. Your response to these questions is your application.
We are a growing U.S.-based short-term rental company. This is a long-term role with room to grow for the right person.
