Guest Communication Specialist

Company Overview

Trust First Management - Why Join Us? (This isn’t your average job ad.)

We’re not looking for someone to just fill a role.

We’re looking for A-Players who want to be part of something big, something that’s moving fast, breaking records, and rewriting what “great” looks like in the short-term rental industry.

We manage 30+ high-performing vacation rentals with an average guest rating of 4.93+ (translation: we don’t do average). Our mission is to deliver exceptional guest and owner experiences every single time while scaling smart to hit $5 million in total booking revenue in the next 6 months.

Position Summary

We’re looking for a fast, detail-oriented Guest Communication Specialist to manage all guest messaging across our portfolio of short-term rental properties.

In this role, you will be responsible for delivering a seamless, high-quality guest experience from booking to checkout while protecting the company’s time, revenue, and reputation. This is not a passive customer service role. You are expected to think critically, solve problems quickly, and act with urgency in a fast-paced environment.

What You’ll Do

• Respond to all guest messages across Airbnb, Booking.com, Hopper, VRBO, and direct bookings

• Maintain fast response times (target: under 5 minutes during scheduled shifts)

• Communicate in a warm, professional, and efficient tone

• Handle pre-booking questions, check-in instructions, and post-stay follow-ups

• Troubleshoot guest issues in real time (WiFi, access, cleanliness, etc.)

• Coordinate with cleaners, maintenance, and operations teams as needed

• Follow company SOPs for refunds, discounts, and escalations

• De-escalate guest concerns and protect review ratings

• Manage early check-in and late checkout requests

• Ensure all reservation details are accurate and complete

• Send scheduled messages and monitor automations for accuracy

• Document all actions clearly in Guesty

• Create and track operational tasks through completion

• Monitor guest satisfaction throughout each stay

• Identify and resolve issues before they impact reviews

• Help maintain a consistent 5-star guest experience

Required Qualifications

• Strong written English skills (clear, natural, and professional communication)

• Experience managing guest communication on Airbnb or similar platforms

• Ability to multitask and manage multiple conversations at once

• High attention to detail with strong accuracy

• Fast decision-making and problem-solving ability

• Reliable internet and ability to work scheduled shifts

Compensation, Benefits & More

Compensation: $5/hour

• Bonus: Performance-based opportunities may be available

• Benefits: Opportunity to grow with a fast-scaling company

• Schedule: Shift-based schedule with high responsiveness expectations

• Job Type: Contractor

• Location: Remote, Philippines (must have reliable internet connection)