Short-Term Rental Guest Experience Specialist

Description

We're building a smarter, more scalable short-term rental business, and we're looking for someone who wants to help us get there.

Our portfolio currently includes three properties, with plans to grow. We're seeking a proactive Short-Term Rental Guest Experience Specialist who can own daily operations, deliver exceptional guest experiences, and build the processes and automations that make everything run more efficiently. You’ll work directly with the founder, learn how the business operates from the inside, and take real ownership of day-to-day operations and growth initiatives.

We want someone who thinks like an operator, solves problems independently, and enjoys improving how things work.

We use Hospitable (PMS), PriceLabs, Turno, Google Sheets, and WhatsApp. We’ll provide training.

We take our work seriously, but not ourselves. Expect high standards, open communication, room to experiment, and an environment where good ideas are welcome regardless of who brings them.

What We're Looking For

Must-Haves

• Hands-on experience in short-term rentals, Airbnb operations, property management, or a closely related hospitality role.
• Excellent written and spoken English, with a friendly, polished, and guest-focused communication style.
• Strong operational judgment, organization, attention to detail, and follow-through.
• Ability to independently troubleshoot problems, prioritize urgent requests, and recognize when to escalate.
• Confidence learning and managing software, spreadsheets, and cloud-based workflows.
• Proactive mindset: you don't just identify problems; you bring solutions.
• Reliable internet, a professional remote-work setup, and availability during agreed working hours.

Big Plus If You Have

• Experience with Hospitable, Turno, PriceLabs, Airbnb, Vrbo, or Booking.com.
• Experience developing SOPs, automations, or operational workflows.
• Familiarity with AI tools and using them responsibly to improve productivity.
• Experience with direct bookings, revenue optimization, invoicing, or payment follow-up.
• Previous experience supporting U.S.-based short-term rental businesses.

You'll Thrive Here If...

• You take ownership. If something needs attention, you take initiative and see it through.
• You're resourceful. You enjoy figuring things out rather than waiting for instructions.
• You're hospitality-minded. You can turn a frustrating guest experience into a positive one.
• You love systems. Repetitive manual work makes you wonder, "How can we automate this?"
• You're accountable. You communicate clearly, follow through, and own your mistakes.
• You're coachable. You welcome feedback, share ideas, and continuously improve.
• You bring positive energy. You can work hard, have fun, and contribute to a supportive team environment.

Schedule & Compensation

• Work Arrangement: 100% remote
• Hours: Full-time, 40 hours per week
• Schedule: Agreed working hours with U.S. time-zone overlap; occasional evening or weekend coverage may be scheduled as needed, with clear boundaries and backup procedures.
• Compensation: 55,000-110,000 (depending on experience)
• Engagement: Long-term independent contractor

Responsibilities

• 1. Guest Experience & Reservations
• Own guest communications across Airbnb, Vrbo, Booking.com, and other booking channels, from inquiry through checkout.
• Deliver warm, professional, and timely support, with a target response time of 15 minutes or less during assigned coverage hours.
• Resolve guest concerns, troubleshoot property issues, and escalate situations requiring owner approval.
• Manage guest reviews, coordinate special requests, and identify appropriate upsell opportunities, including early check-in and late checkout.
• 2. Property Operations & Vendor Coordination
• Coordinate cleaning schedules, turnovers, property readiness, and maintenance vendors.
• Maintain inventory, order supplies within approved budgets, and ensure properties remain guest-ready.
• Manage cleaning checklists, communicate performance feedback, and follow issues through resolution.
• Identify recurring operational problems and implement improvements to prevent them.
• 3. Systems, Automation & Process Improvement
• Become our go-to expert on Hospitable, including reservation workflows, guest messaging, integrations, and troubleshooting.
• Build practical SOPs, checklists, and workflows that support consistent operations.
• Identify opportunities to use AI, automation, and technology to reduce manual work and improve service.
• Maintain accurate operational records and develop repeatable systems that can support additional properties.
• 4. Revenue & Growth Support
• Based on experience and as operational capacity allows:
• Assist with PriceLabs pricing rules and seasonal adjustments within approved guidelines.
• Maintain and optimize property listings, descriptions, amenities, and booking-channel information.
• Help develop direct-booking capabilities and identify opportunities to improve occupancy, guest satisfaction, and revenue.
• Support other operational and growth initiatives as the portfolio expands.

Experience

1 Year

Apply By

Dec 9, 2026

Required Skills

• Reservation and booking management
• Property Management Systems (PMS)
• Check-In And Check-Out Coordination
• Housekeeping And Maintenance Coordination
• Service recovery
• Guest Communication
• Accountability
• Problem Solving
• Proactivity
• Organization
• English Communication

Nice to Have Skills

• Adaptability
• Time management
• Turno
• Pricelabs
• Hospitable
• Channel manager synchronization across Airbnb, Vrbo, and Booking.com
• Automated guest messaging and check-in workflows
• Property Management System (PMS) proficiency