Guest Operations Manager (AI-Assisted, Vacation Rentals)

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: TYPE OF WORK

Full Time

: SALARY

$7-9

: HOURS PER WEEK

40

: DATE UPDATED

Jan 29, 2026

JOB OVERVIEW

Guest Operations Manager (AI-Assisted, Vacation Rentals)
Villa Paraiso Vacation Rentals (Miami + Florida Keys)
Remote | Philippines

Pay: $7 to $9 USD/hour starting (based on Guesty operations skill)
Schedule: Friday to Tuesday, 10:00 AM to 5:00 PM US Eastern Time
Philippines time: This is usually 11:00 PM to 6:00 AM Manila time (night shift)

About Us
We manage 20+ luxury waterfront vacation rentals in Miami and the Florida Keys.
We run on systems, SOPs, and accountability. Guest messaging is largely automated using HostBuddy AI, so your job is NOT to sit there typing all day.
Your job is to resolve real issues, coordinate the field team, and keep operations clean and on-track.

The Role (What you’ll actually do)
You are the “closer” for daily ops.
HostBuddy AI covers most routine guest communication. You handle escalations, coordination, and follow-through.

Core Responsibilities
1) Issue Resolution and Guest Support (Primary)
- Monitor HostBuddy AI escalations and identify what needs a human
- Handle urgent issues end-to-end: lockouts, WiFi, AC, hot water, noise complaints, access issues
- Coordinate solutions with cleaners, maintenance vendors, and field team
- Keep the guest calm, set expectations, and close the loop once fixed

2) Turnover and Team Coordination
- Confirm checkouts and coordinate cleanings, inspections, and same-day turns
- Handle last-minute changes: late checkouts, early check-in requests, schedule shifts
- Ensure every turnover is completed on time and meets quality standards

3) Systems Management (Guesty + Breezeway)
- Maintain Guesty: reservation changes, guest notes, tasks, internal status updates
- Create and track Breezeway tasks for housekeeping, inspections, maintenance
- Keep trackers updated (Google Sheets) so nothing gets lost
- Flag when automations break and report what happened clearly

Tools You’ll Use
Guesty, Breezeway, HostBuddy AI, ---------- , Google Workspace, Slack, ChatGPT

Must-Haves (Read carefully)
- 1+ year experience in short-term rental operations, hospitality ops, or property management
- Guesty experience required (real daily use, not “familiar”)
- Strong written English (you will message guests when escalation happens)
- Calm under pressure and good judgment (you don’t panic, you execute)
- Strong follow-through (you close loops and document outcomes)
- Reliable internet + quiet setup (headset, stable computer)
- Full focus during your shift (no other client work during live guest support hours)

Nice to Have
- Breezeway experience
- Vendor coordination experience
- Familiar with STR tools and automations (Zapier/Make/n8n)

After-Hours
Rare (about 1 to 2 times per month), only for true urgent issues like lockouts or emergencies. You are not on-call 24/7.

Training
You will get structured onboarding on our properties, SOPs, and systems before running shifts solo. We want you confident, not guessing.

Growth Path
Top performers can advance to Operations Manager within 12 to 18 months (higher pay, more ownership, team oversight, owner communications, and system projects). Raises are performance-based.

How to Apply (Required)
Start your application message with: Keys Ready
Attach your resume and answer ALL questions below (copy/paste the questions with your answers).

Application Questions
1) Confirm availability: Can you work Friday to Tuesday, 10 AM to 5 PM Eastern Time every week? Yes/No
2) Confirm night shift: What is that schedule in Manila time for you, and are you comfortable long-term? Yes/No
3) Guesty proof: How long have you used Guesty, and what were the last 3 tasks you did inside it?
4) Escalation scenario: Guest says “AC is not working, it’s 85 degrees inside.” Walk through exactly what you do step-by-step.
5) Lockout scenario: Guest is locked out at 9 PM. What do you do step-by-step?
6) Turnover pressure: Cleaner says “Is checkout extended for Unit 7?” and you have a same-day check-in. What do you do and how do you prevent delays?
7) Internet: Paste your download/upload speed and confirm you have a backup internet option.
8) Self-awareness: What part of this job would be hardest for you, and how would you handle it?

Applications that skip questions will not be reviewed.

SKILL REQUIREMENT

Property Management Short Term Rentals Airbnb

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Guest Operations Manager (AI-Assisted, Vacation Rentals)

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

TYPE OF WORK

SALARY

HOURS PER WEEK

DATE UPDATED

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