Vacation Rental Operations Manager - Guest Operations & Remote Team Leadership

We are a growing vacation rental property management company managing properties across Tennessee, Texas, and Indiana. We handle guest experience, owner relationships, and property performance for a multi-property portfolio. We are not asking you to build operations from scratch. We already have procedures, a remote guest communications team, property management technology (Hostfully), pricing systems (PriceLabs), and established workflows. We need someone to own the daily execution of that operation, hold it to a standard, and make it steadily better. This is a long term position. We are looking for someone who wants to stay and grow with us, not fill a gap for six months. THE CORE PROBLEM YOU ARE SOLVING Right now, things get reported as done before anyone confirms they actually work. A message template breaks and runs for weeks before someone notices. A team member leaves and the knowledge in their head leaves with them. A guest issue gets a task created and everyone assumes it is handled. Your job is to close that gap. Not by doing every task yourself, but by making sure the right person does each task correctly, it gets verified, and it gets written down so the next person can pick it up. If you are the kind of person who checks that the fix actually worked before calling it done, keep reading. WHAT YOU WILL OWN 1. Guest Communications Team Management Directly manage our remote guest communications team. Build and maintain schedules, shift coverage, handoffs, and escalation coverage across time zones. Track attendance, response times, resolution times, missed messages, and communication quality. Coach people who are struggling, recognize people doing well, and hold the standard consistently. Make sure critical information actually moves between shifts instead of getting dropped. 2. Guest Experience and Issue Resolution Own guest communication quality and outcomes. Monitor unanswered messages, complaints, refund requests, maintenance issues, and anything heading toward a bad review. Define clearly what the team can resolve on their own, what comes to you, and what needs owner approval. Handle escalations: credits, relocations, early check-ins, late checkouts, OTA disputes, and difficult guests. 3. Incident Coordination When something goes wrong, you run it. Lead response on lockouts, outages, HVAC and plumbing failures, double bookings, safety issues, and service failures. Coordinate across guest communications, housekeeping, maintenance, and ownership with a clear owner and deadline for every action. Follow up until it is actually resolved, then document what happened and what prevents it next time. 4. Quality Assurance and Documentation This is the part that matters most to us. Audit guest conversations, automated messages, property information, and system records regularly. Find problems before guests, owners, or leadership find them. Write down and maintain the procedures. Anything you own must be documented well enough that someone else could pick it up tomorrow. Learn how something works before you change it, then change it, verify it worked, and document what changed. 5. Systems Accuracy (Hostfully and related tools) You do not need to be a developer, but you need to be genuinely competent in our systems. Become highly proficient in Hostfully: reservations, calendars, automated messaging, property configuration, tasks, and reporting. Keep property details accurate: amenities, sleeping arrangements, check-in instructions, house rules, contacts. Treat stale or wrong information as an operational problem, because automated systems are only as good as what you feed them. Flag pricing, listing, and revenue issues you spot to leadership. You are not expected to own revenue strategy, but you are expected to notice when something looks wrong. 6. Working With AI Tools We are building AI and automation into our operation over the coming year. You should be comfortable using tools like ChatGPT and Claude in your daily work. As we roll out automation, you will help test it, spot where it gets things wrong, and tell us honestly whether it is helping or adding noise. We are not asking you to build AI systems. We are asking you to use them well and give us straight feedback. FIRST 90 DAYS Days 1-30, learn and verify. Train on our current procedures, team structure, escalation rules, and systems. Build working relationships. Observe before changing anything. Give us an honest baseline of what is working and what is not, including things we may not want to hear. Days 31-60, own the daily operation. Take clear ownership of team accountability, escalations, and issue follow-through. Start fixing the highest impact gaps you found in month one. Begin documenting what is currently undocumented. Days 61-90, improve and prove it. Deliver measurable improvements with before and after numbers. Establish a steady weekly management rhythm. Show us that things are getting caught earlier than they used to be. REPORTING RHYTHM Daily: urgent guest issues, coverage risks, anything needing an owner decision. Weekly: team performance numbers, guest communication metrics, open incidents, recurring problems, recommended actions. Monthly: trends, root causes, what improved and by how much. We want reporting that drives decisions, not reports for the sake of reports. WHAT WE NEED FROM YOU Required: Real experience managing vacation rental or hospitality operations across multiple properties. Direct experience managing remote teams: scheduling, performance, coaching, accountability. Solid working knowledge of Airbnb, Vrbo, and Booking.com operations. Experience with a property management system. Hostfully experience is a strong plus. Excellent written English. You will be writing to guests, owners, and your team every day. Strong follow-through. You finish what you start without being chased. Helpful but not required: PriceLabs or similar dynamic pricing exposure. Experience improving listings or conversion. Experience documenting SOPs from scratch. WHO THIS IS NOT FOR Someone who needs constant direction or waits for problems to be pointed out. Someone whose experience is guest messaging only, with no broader operations responsibility. Someone uncomfortable holding teammates accountable or making judgment calls. Someone who replaces procedures before understanding why they exist. Someone who reports things as done without confirming they work. COMPENSATION AND GROWTH 8.00 USD per hour, full time, long term. We are direct about this: this rate reflects a focused operations role, not a portfolio wide executive position. What we offer alongside it is stability, a genuine long term seat, real ownership of your area, and early exposure to AI and automation work that most operations roles will not touch for years. As the operation grows and you prove out, scope and compensation grow with it. We would rather find one person who stays for years than cycle through hires. HOW TO APPLY Start your proposal with TRUEPMG OPERATIONS, then answer these directly and specifically. Short, concrete answers beat long general ones. 1. How many years have you worked in vacation rental or property management operations? 2. What is the largest portfolio you have managed or helped manage at one time? 3. Which property management system have you used, and what did you do in it day to day? 4. How many remote team members have you directly supervised, and how did you measure their performance? 5. Which OTAs have you managed operations for? 6. Describe a serious guest or operational incident you personally coordinated. What happened, what did you do, and what changed afterward? 7. Tell us about a time you found a problem nobody else had noticed. How did you find it? 8. How do you make sure something is actually fixed and not just reported as fixed? 9. How are you currently using AI tools in your work? 10. What would you focus on in your first 30 days here? Video required: Include a 2-3 minute Loom video. Introduce yourself, describe your vacation rental operations experience, how you manage remote teams, and how you would approach taking over an operation that already exists. Applications missing the written answers or the video will not be reviewed.