AI-Enabled Guest Operations Coordinator (Vacation Rentals)

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TYPE OF WORK

Full Time

SALARY

$7.50/hr training; $8.25/hr confirmed

HOURS PER WEEK

35

DATE UPDATED

Jul 30, 2026

JOB OVERVIEW

Villa Paraiso Vacation Rentals | Remote, Philippines | Long-term growth role

Schedule: Friday-Tuesday, 10:00 AM-5:00 PM US Eastern Time
Philippine time: Usually 10:00 PM-5:00 AM during US daylight saving time and 11:00 PM-6:00 AM during US standard time
Days off: Wednesday and Thursday
Hours: 35 guaranteed hours/week
Pay: $7.50 USD/hour during 30-60 days of paid training; $8.25/hour after confirmation against the role scorecard; growth up to $8.75/hour after six months for strong performance

ABOUT VILLA PARAISO

Villa Paraiso Vacation Rentals manages approximately 20 luxury waterfront vacation homes in the Florida Keys. We use AI, clear procedures, and a local field team to deliver excellent guest stays and keep daily operations organized.

We are not looking for a senior property manager or someone who already knows every vacation-rental platform. We want someone early in their career who is hungry, articulate, highly coachable, and already uses AI seriously.

We will teach you our properties, Guesty, Breezeway, Trellis, and our operating procedures. You bring strong spoken English, curiosity, follow-through, hospitality judgment, and proof that you can use AI without blindly trusting it.

WHAT YOU WILL DO

Guest communication and issue resolution
- Monitor AI-assisted guest communication and recognize when a human needs to step in.
- Speak and write with guests clearly, warmly, and professionally.
- Help resolve access, Wi-Fi, AC, maintenance, check-in, checkout, and property questions.
- Keep the guest informed, coordinate the solution, and confirm the issue is actually closed.

Daily operations
- Review arrivals, departures, turnovers, maintenance, and urgent follow-ups.
- Coordinate cleaners, maintenance vendors, and local field support.
- Keep tasks, notes, photos, receipts, costs, approvals, and resolution details organized.
- Escalate safety, financial, or high-risk guest situations early and clearly.
- Produce a concise shift handoff showing what is open, resolved, or waiting.

AI-enabled work
- Use ChatGPT, Claude, Gemini, Perplexity, or similar tools to summarize guest issues, improve drafts, structure information, research solutions, and improve workflows.
- Check AI output for incorrect facts, unsafe recommendations, missing context, and inappropriate tone before using it.
- Protect guest, owner, and company information when using AI.
- Notice repetitive work and suggest a better prompt, checklist, template, or automation.

WHAT WE REQUIRE

- At least some hands-on short-term rental operations experience. This can include Airbnb/Vrbo guest communication, reservations, turnovers, cleaner/vendor coordination, property readiness, or work in Guesty, Hostaway, Hospitable, Breezeway, or a similar STR system.
- Clear, confident spoken English and strong written English.
- Real experience using AI for work, school, projects, or your own business. You must be able to show your prompt, the output, what you corrected, and what you verified.
- Good judgment, curiosity, and willingness to ask questions instead of guessing.
- Strong follow-through: you keep working an issue until it is resolved, documented, or properly escalated.
- Comfort speaking with US guests, cleaners, vendors, and coworkers.
- Reliable computer, quiet workspace, primary internet, backup internet, and a practical power-outage plan.
- Full long-term availability for the exact Friday-Tuesday night schedule, including US daylight-saving changes.
- No conflicting client work during scheduled live-support hours.
- Willingness to complete job-relevant identity, NBI clearance, employment, and reference verification after a conditional offer and with written consent.

HELPFUL, NOT REQUIRED

- Experience supporting multiple short-term rentals or handling live guest escalations.
- Guesty, Breezeway, Hostaway, Hospitable, PriceLabs, or similar tools.
- Google Sheets, task-management software, documentation, or simple automations.

We would rather hire someone with real STR fundamentals who is hungry and highly coachable than a senior operator who has stopped learning.

WHAT SUCCESS LOOKS LIKE

First 30 days
- Learn our homes, standards, escalation rules, and daily rhythm.
- Draft accurate guest and vendor communication with review.
- Keep assigned tasks and handoffs complete.
- Demonstrate safe, practical AI use instead of copying output blindly.

By 60-90 days
- Handle routine guest issues and turnover follow-up independently.
- Coordinate cleaners and vendors calmly under time pressure.
- Maintain accurate records with complete supporting proof.
- Improve at least one recurring workflow using AI, documentation, or automation.

Strong performers can grow into broader operations, owner reporting, quality control, automation, and eventually operations-management responsibility. Growth is based on judgment and outcomes, not just time in the role.

HIRING PROCESS

1. OnlineJobs.ph application, resume, written answers, and video introduction.
2. Structured interview and short live guest role-play.
3. Paid 60-90 minute AI-enabled operations exercise using fictional information.
4. Conditional offer and consent-based background/reference verification.
5. Paid onboarding.

HOW TO APPLY

Use the subject line: AI OPS - [Your Full Name]

VIDEO IS MANDATORY. Applications without a public, accessible 60-90 second camera-on video will not be accepted or reviewed. Please test the link in a private/incognito window before submitting.

BONUS / DIRECT APPLICATION

For extra consideration, visit the official Villa Paraiso Vacation Rentals website and choose Careers, then Remote Short-Term Rental Operations Assistant. OnlineJobs.ph hides external URLs, so use the Careers link in our website footer.

You may use the same resume and video. Completing the direct form is optional bonus consideration; the video itself is required for every applicant.

Send:
1. Your updated resume.
2. A public 60-90 second Loom or Google Drive video. Camera on, speak naturally, and do not read a script. Tell us:
- Why this schedule and role fit you.
- One real example of how you used AI to solve a problem or improve your work.
3. Answer the questions below concisely. Keep the total written response under 700 words.

APPLICATION QUESTIONS

1. Confirm you can consistently work Friday-Tuesday, 10:00 AM-5:00 PM US Eastern Time. What exact hours is that where you live during both US daylight saving time and standard time?
2. Which AI tools have you used? Share one privacy-safe example with: your prompt, a short raw-output excerpt, your corrected final result, and what you independently verified.
3. An AI assistant drafts a confident response to a guest, but one property fact may be wrong. What do you do before sending it?
4. A guest arrives in two hours. The cleaner has not confirmed completion, the AC may not be cooling, and three other guests are waiting for replies. Walk us through your first 30 minutes.
5. Tell us about a time you learned a new tool or process quickly. How did you make sure you could repeat the work correctly later?
6. Tell us about an error or missing detail you caught before it became a larger problem. What did you do?
7. Describe your computer, primary internet, backup internet, and power-outage plan.
8. If selected as the conditional finalist, are you willing to authorize job-relevant reference and background verification and provide a recent NBI clearance? Yes or no.

Do not include sensitive client, guest, or employer information in your examples. Applications missing the video or questions will not be accepted or reviewed.

Villa Paraiso welcomes applicants from every background. We evaluate communication, judgment, integrity, learning ability, and work samples - not accent, age, or a perfect resume.

SKILL REQUIREMENT
Property Management Customer Service Artificial Intelligence
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