Description
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: $5.00/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)