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TYPE OF WORK
Full Time
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SALARY
$5-9 hour
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HOURS PER WEEK
35
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DATE UPDATED
Jan 27, 2026
AI-Powered Guest Operations Specialist
Villa Paraiso Vacation Rentals
Remote | Latin America & Philippines Candidates Preferred
Schedule: Friday–Tuesday, 10:00 AM–5:00 PM ET (flexibility for occasional after-hours needs)
Rate: $5–10/hour USD based on experience | Growth Path to Operations Manager
About Villa Paraiso
We're a luxury vacation rental company managing 20+ premium waterfront properties across Miami and the Florida Keys. We operate with an AI-forward mindset—leveraging automation, smart workflows, and cutting-edge tools to deliver exceptional guest experiences at scale. We need someone who thrives in that environment.
The Role
This isn't a "just answer messages" position. You'll be the operational backbone of our guest experience—working independently, solving problems in real-time, and keeping our properties running smoothly. You'll use AI tools daily, manage multiple systems, and help us continuously improve how we operate.
What You'll Do
Guest Operations (60%)
Respond to guest inquiries across Airbnb, VRBO,
Handle check-in/check-out coordination, guest requests, and issue resolution
Manage reservation modifications, cancellations, and special requests in Guesty
Monitor and respond to guest reviews
Systems & Workflow Management (25%)
Maintain Guesty PMS—reservations, listings, messaging, and reporting
Coordinate tasks in Breezeway for housekeeping, inspections, and maintenance
Keep Google Sheets, trackers, and internal documentation updated and accurate
Flag system issues and help troubleshoot when automations break
AI-Enhanced Operations (15%)
Use ChatGPT, Claude, and AI tools to draft responses, solve problems, and work faster
Learn and adapt to new tools quickly as we evolve our tech stack
Identify opportunities to automate repetitive tasks
Vendor & Team Coordination
Route maintenance requests, housekeeping issues, and service calls to our contractor network
Communicate with field team on property needs and urgent situations
Track open issues to completion
You're a Great Fit If You Have:
Must-Haves:
1-2+ years in short-term rental operations (vacation rentals, property management, or hospitality)
Guesty PMS experience—non-negotiable (you should know it inside and out)
Fluent Spanish and strong English communication skills
Comfortable using AI tools (ChatGPT, Claude) and learning new technology quickly
Highly independent—you see what needs to be done and handle it without being asked
Reliable internet and professional remote work setup
Strong Bonus Points:
Breezeway experience (or similar task management platforms)
Familiar with HostBuddy, StayFi, or other STR tools
Experience with automation platforms (n8n, Zapier, Make)
Background in hospitality or customer service excellence
What We Offer
Clear growth path to Operations Manager for top performers
Work with cutting-edge AI tools and help shape our automation strategy
Autonomy and ownership—no micromanagement, just accountability
Fast-paced environment where your problem-solving skills actually matter
Exposure to luxury hospitality in Miami and the Florida Keys
Not a Fit If:
You need constant supervision or step-by-step instructions
You're uncomfortable with technology or resistant to learning new tools
You prefer slow-paced, predictable work
You don't have hands-on Guesty experience
Prescreening Questions (Please Answer in Your Application):
How many years of Guesty experience do you have? Which features have you used most?
Describe a time you handled a difficult guest situation. What happened and how did you resolve it?
What AI tools do you currently use in your work? Give a specific example of how you've used them.
A guest messages at 7 PM saying their AC isn't working and it's 85 degrees inside. Walk me through exactly what you would do.
What does "working independently" mean to you? How do you stay on top of tasks without someone checking in on you?
What is your internet speed (upload/download) and do you have a backup if it goes down?
Are you available to work Friday through Tuesday, 10 AM to 5 PM Eastern Time?
To Apply:
Send your resume and answers to the prescreening questions above.
Important: Include the word "manatee" in the subject line of your application so we know you read the full posting.
We review applications on a rolling basis. Top candidates will be contacted within 48 hours.
