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.

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.

• Respond to all guest messages across Airbnb, , 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

• 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: $5.00/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)