Customer Service Lead (Airbnb / Short-Term Rental)

DO NOT APPLY IF YOU DO NOT HAVE AIRBNB MANAGEMENT EXPERIENCE WavyStay is a Washington DC-based remote short-term rental co-hosting and property management company. Since 2021, we have managed 40–100+ properties across the US. We run a remote-first team with a Philippines-based virtual operations team, an AI-powered guest communication system, and a tech stack built around Hospitable,Slack, Monday.com, GoHighLevel, and HostBuddy AI. Our current Operations Lead is transitioning out of the role. We are looking for an experienced, self-directed STR operations professional to step in and own the day-to-day management of our guest services team. This is one of the most important roles in our company. If you are organized, decisive, and have real experience managing remote teams in the short-term rental space, we want to hear from you. ABOUT THE ROLE The Operations Lead is the backbone of WavyStay's daily execution. You sit between the CEO and the Customer Service team translating strategy into action, keeping the team accountable, and making sure nothing falls through the cracks across 40+ active properties. You will not be doing daily guest messaging. We use HostBuddy AI for that. Your job is to make sure the team and the systems are running at the highest level every single day. WHAT YOU WILL DO TEAM OVERSIGHT & SCHEDULING - Own daily oversight of the CS team shift checklists and schedule adherence - Ensure inbox coverage, phone line coverage, and calendar management are never gaps - Monitor team performance in real time and flag issues before they become problems - Run the weekly team meeting keep it on agenda, on time, and action-oriented PERFORMANCE & REPORTING - Compile the weekly team KPI scorecard and deliver it to the CEO every Monday morning - Track guest review scores, response times, open maintenance items, and claim resolution rates - Identify performance trends and recommend corrections before they impact guest experience - Maintain accountability logs for each team member AI SYSTEM MANAGEMENT - Oversee HostBuddy AI configuration and message quality - Spot-check AI responses daily and flag any responses that need human override - Update AI knowledge base when property details, access codes, or house rules change - Work with the CEO to optimize AI performance as the portfolio scales VENDOR & CLEANING MANAGER RELATIONSHIPS - Serve as the primary point of contact for cleaning managers (CMs) and maintenance manager - Conduct daily check-ins with CMs to confirm turnover completions and flag issues - Coordinate urgent maintenance and repair requests across the portfolio - Track vendor performance and escalate recurring issues ESCALATION HANDLING - Serve as the first escalation point for the CS team on operational blockers, system access issues, and coverage gaps - Handle high-priority guest issues that require management-level intervention - Coordinate AirCover and damage claim submissions alongside the Claims Manager - Own resolution on any issue the CS team cannot resolve independently TEAM DEVELOPMENT - Conduct retraining when performance gaps are identified - Issue corrective action when needed and recommend termination when warranted - Onboard new CS team hires and ensure they are up to speed on SOPs before going live - Maintain and update operational SOPs when recurring issues require process changes WHAT YOU NEED - 2–5 years of experience in STR operations, property management, or remote team management - Direct experience with Airbnb, VRBO, Hospitable or a multi-listing STR management company - Proven ability to manage a remote team across multiple time zones - Strong written and verbal English communication - Experience with guest communication platforms (Hospitable, Guesty, OwnerRez, or similar) - Comfortable working inside CRM and project management tools - Highly organized with a bias toward documentation and systems - Available 9:00 AM – 6:00 PM EST, Monday through Sunday with weekend availability for escalations ; Will have multiple days off throughout the week. BONUS POINTS - Experience with HostBuddy AI, Hostpitable, Monday.com and GoHighLevel - Prior experience managing 20+ STR listings simultaneously - Background in team coaching, performance management, or CS quality auditing - Experience handling Airbnb AirCover claims and damage disputes and airbnb resolutions COMPENSATION Base salary: $600–$1,000/month USD depending on experience Performance bonus tied to team KPI achievement 90-day review with raise potential Long-term role we are building for scale and want someone who grows with us HOW TO APPLY Do not send a template application. We will not read it. To be considered, send all three of the following: 1. Your resume or OnlineJobs.ph profile link 2. A 2–3 minute video introduction tell us who you are, the largest STR portfolio or team you have managed, and one specific example of a time you caught a problem before it became a guest complaint 3. Answer this question in writing: "It is Saturday morning at 9AM EST. Two cleaning managers have not confirmed their turnovers, one team member called out sick, and a guest just messaged saying they cannot get into the property. Walk me through how you handle the next 30 minutes." All three items are required. Missing any one means your application will not be reviewed. This role requires someone who can hold the operation together when things get chaotic — and in STR, they always do. Show us how you think. — The WavyStay Team wavystay.com