Hospitality Operations (Airbnb / Short-Term Rentals)

Remote – Decision-Based Role, Not Scripted Customer Service

Sunday–Friday, 8 AM– 4 PM PST | Saturdays off

About the Role

We operate a portfolio of short- and long-term rental properties and are looking for a Hospitality Operations Manager to act as the first line of decision-making for guest communication and daily operations.

This role is not basic customer service. It requires logical thinking, calm judgment, persuasion, and the ability to protect revenue while maintaining strong guest experiences. You will be trusted to make decisions, not just follow scripts.

Core Responsibilities

1. Guest Communication & Booking Conversion

Respond to guest inquiries with persuasive, confident, and professional messaging. Convert inquiries into bookings without sounding desperate or robotic. Identify red flags before booking and escalate when needed. Set clear expectations to prevent future issues.

2. Issue Resolution & Judgment Calls

Handle guest concerns (noise, cleanliness, amenities, maintenance, refunds). De-escalate emotional situations while upholding house rules. Determine appropriate remedies within approved limits — not automatic refunds. Ask clarifying questions before offering compensation.

3. Operations Coordination

Coordinate cleaners, maintenance, and vendors. Prioritize urgent vs. non-urgent issues. Ensure fast, clear communication between all parties. Close the loop and confirm resolution with guests.

4. Revenue & Review Protection

Balance guest satisfaction with business profitability. Avoid unnecessary refunds, discounts, or policy violations. Protect review scores through proactive communication and expectation management. Recognize when goodwill gestures are warranted — and when they are not.

Decision Authority

You will be authorized to offer goodwill credits and refunds within defined limits, make real-time judgment calls without waiting for approval, and escalate only when situations exceed your authority or involve legal/safety risk.

What Success Looks Like

High response speed paired with high-quality responses. Fewer escalations to the owner. Lower refund frequency. Consistent 5-star reviews. Guests feel heard — even when told "no."

Who This Role Is NOT For

Script-only customer service reps. People who escalate every gray situation. Candidates afraid of making mistakes. Anyone who needs step-by-step instructions for every scenario.

Requirements

Fluent English, written and spoken

Experience with Airbnb

Logical decision-making and problem-solving ability

Resourceful — able to Google, YouTube, or ask in order to solve issues

Emotional intelligence and calm under pressure

Attention to detail

Strong multitasker

Must have a Mac AND an iPhone 13 or higher

Must work exclusively for me during scheduled hours

How to Apply

Read these instructions carefully. How you apply is the first test.

Include the word “Pineapple” as the first word in your application.

In the body of the email, include all four of the following:

A short paragraph introducing yourself and why this role fits you.

Your Airbnb experience (hosting, co-hosting, managing for others — be specific).

Your current time zone and confirmation you can work Sunday - Friday, 8 PM– 4 PM PST.

Your response to this scenario: A guest messages you at 9 PM saying they just arrived at the property and the Wi-Fi isn't working. Write the exact message you'd send back to them.

Applications missing any of the four items above, or without the correct subject line, will not be reviewed. I'm hiring quickly — show me you're the type of person who takes initiative, reads carefully, and cares about doing great work.

PS. NO AGENCIES. Please do not apply.