Guest Support & Operations Specialist | Luxury Vacation Rentals

Title: After-Hours Guest Support & Operations Specialist | Luxury Vacation Rentals Schedule: Part-time, approximately 30–35 hours/week. Required coverage is 6 PM–1 AM Eastern Time, including scheduled Friday, Saturday, and Sunday shifts. You must be actively available throughout each assigned shift; this is not passive on-call work. Responsibilities • Monitor and respond to Airbnb, Vrbo, Booking.com, Hostfully, email, and approved guest communication channels. • Acknowledge all new guest messages within 5 minutes during your shift. • Handle evening arrivals, guest questions, lockouts, urgent requests, and issue triage calmly and professionally. • Dispatch or escalate approved vendors for urgent maintenance issues, then document actions and status in Breezeway and Slack. • Follow up on cleaning, turnover, and maintenance items; maintain accurate property notes and calendar status. • Complete a structured end-of-shift handoff listing open guest issues, vendor status, actions taken, promised follow-ups, and deadlines. • Assist with reviews, guest feedback, and routine administrative tasks when guest volume is low. Requirements • Excellent written English and confident phone communication. • Laptop-based work environment, reliable internet, and backup connectivity. • Hubstaff must run throughout paid shifts; paid time must be supported by scheduled availability, role-related work, documented outputs, and response-time performance. • Experience in vacation rentals, hotels, guest support, dispatch, or property operations is strongly preferred. • No other work or personal obligation may interfere with required coverage. Compensation: $8–$12/hour, based on experience, English fluency, and proven after-hours guest-support capability. Long-term role with performance-based growth. ⚠️ IMPORTANT NOTICE FOR APPLICANTS: DO NOT call our guest support phone numbers or 800 lines. Our phone lines are strictly reserved for active guests and emergency property support. Candidates who attempt to call our guest lines will be immediately disqualified and blocked from consideration. All applications and communications must remain strictly through Upwork. Required application 1. A 30–60 second Loom video or voice note introducing yourself and describing relevant hospitality/customer-support experience. 2. Your exact availability in US Eastern Time, including Friday, Saturday, and Sunday evenings. 3. A written response: “At 11:30 PM, a guest says they cannot enter the home. What are your first three actions?”