Vacation Rental Specialist - Team Lead

About Us
We’re Extenteam, a dynamic company revolutionizing the short term vacation rental industry. Our proven business model has generated consistent revenue, and we are now expanding from a professional services model to a scalable tech-based subscription-first model.

As a scaling stage startup, we aim to grow our Monthly Recurring Revenue (MRR) to double our revenue by January 2026 by providing an AI assisted SaaS platform that works for all short term rental businesses regardless of their size.

Extenteam is on a mission to streamline and support vacation rental businesses by providing top-notch solutions, including guest communication and property management support.

We generate revenue through two primary streams:

• Dedicated Team Members: Providing trained overseas talent with a recurring premium model, replacing one-time recruitment fees.
• Tailwind - SaaS Platform: A guest communication Software blended with our shared services team, supporting smaller operators typically with less than 50 units - helping Extenteam increase profitability while growing our product market fit and expanding TAM and service levels.

Extenteam is a small but mighty team of 50 consisting of Sales, Partner Success, Marketing, HR & Recruiting, Engineering, Product and Admin (IT, Data etc). We are spread out across the world but we have hubs in Miami, LA, Medellin, and actively expanding into Europe. Our 50 people core team is supported by 400+ DTMs (dedicated team members) that are servicing our customers.

Our Values:

• Commitment to Excellence: Continuously raising the bar and setting new standards in guest communications and service delivery. 
• Exceptional Collaboration: Thriving in a fast-paced, high-performance environment built on clear communication and teamwork. 
• Unified Purpose: Aligning behind a shared mission to drive success with an intense focus. One shared consciousness. 
• Data-Driven Decision-Making: Prioritizing data and results over emotions when making objective, professional decisions. 
• Emphasis on Details: Details matter at every level. Leaders are expected to have a deep understanding of the specifics and adopt a hands-on management style.

Our Leadership Philosophy

Our company embraces a management style inspired by the ideals of "founder mode," as championed by Airbnb’s Brian Chesky. This means a hands-on, visionary approach to leadership, with a relentless focus on innovation, product excellence, and customer-centric decision-making. We encourage proactive problem-solving, direct involvement in key initiatives, and a collaborative, high-performance culture.

To learn more about the "founder mode" philosophy and how it shapes our operations, you can explore this link. Understanding this mindset will provide valuable context for how we operate and what we value in our team members. 

The Guest Services Specialist (GSS) supports owners by managing reservation-level details, guest inquiries, and listing updates. This role acts as a frontline operator, keeping the day-to-day smooth, resolving technical issues, and looping in Account Managers only when strategic or high-level business questions arise. The GSS is a hybrid of guest-facing precision and internal coordination — providing clarity, minimizing friction, and helping properties run like clockwork. Most importantly: the GSS is a frontline observer of owner sentiment. If an owner starts sounding disengaged, anxious, or frustrated, the GSS must immediately notify the assigned Account Manager.

Examples include:

• A usually responsive owner becomes slow or short in replies
• The tone of their messages shifts to concern or annoyance 
• They mention feeling uncertain about results, systems, or guest experiences Early detection helps preserve trust — and lets the Account Manager step in before it becomes a churn risk. 

Core Responsibilities

1. Review Management

• Monitor and respond to guest reviews (public + auto responses)
• Edit and maintain automated review responses for accuracy and tone
• Escalate any negative reviews to Account Managers with suggested context
• Share review-related feedback with owners to help avoid future issues Example: “Let’s avoid guest complaints about A/C by updating pre-arrival info.”
• Notify owners and Account Managers if a review reveals a maintenance, repair, or service issue that needs resolution 
• Assist owners in managing guest communication when property damage or misconduct occurs, including:  ○ Cancelling or delaying automated guest reviews when appropriate ○ Initiating OTA messaging that prevents negative auto-reviews ○ Ensuring proper claim language is recorded in-platform 

2. Reservation Management 

• Confirm all reservations have completed payment status
• Respond to guest inquiries (pre- and post-booking)
• Process modifications and cancellations based on owner rules
• Notify vendors or cleaners of any changes that impact scheduling
• Help owners file claims through OTAs or 3rd party damage insurance providers when applicable
• Notify owners’ preferred vendors directly when repairs, maintenance, or other services are needed
• Monitor the Guest Comms Master Sheet ○ Ensure every guest thread is visible and tagged correctly ○ Flag odd or incomplete threads for follow-up

3. Listing Management 

• Swap listing photos daily (or per optimization schedule) 
• Monitor photo performance if applicable (using platform insights)
• Support Account Managers and Optimization Team with basic listing updates

4. Owner Support: Guest-Specific Questions

• Guest questions must be answered immediately — use AirINN’s OSM Chatbot (AI) to draft fast responses
• If a guest asks a question that isn’t addressed in the property-specific Master Sheet: ○ Reach out to the owner or Account Manager to get clarity ○ Update the Master Sheet to ensure future questions can be answered instantly
• Help owners manage reservation logistics or platform troubleshooting
• Only escalate to Account Managers if the question involves: ○ Strategy ○ Pricing decisions ○ Performance-level feedback

Key Communication Rules 

• GSS handles guest logistics and tech support; Account Managers own the relationship and strategy
• Always respond in-platform unless directed otherwise
• When messaging owners, always provide context + your proposed solution
• Stay alert to tone changes in owner communication and flag friction early

Daily Workflow Checklist 

• Check and clear guest review inbox
• Flag reviews with repair/service issues to owners + AMs
• Assist with canceling/delaying auto-reviews if there's been a guest issue
• Verify reservation statuses + recent changes
• File any necessary OTA/insurance claims or vendor contacts
• Review guest comms master sheet for new activity
• Scan owner inboxes for forwarded guest questions
• Answer all guest questions immediately using AI when needed
• Update Master Sheets with any missing FAQ responses 
• Review listing photo queue for rotation
• Update vendors if any last-minute changes occur 
• Watch for signs of owner friction and report any red flags to the AM team