Guest Operations Specialist

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. What This Role Is About: We’re looking for a Guest Operations Specialist for a Property management company client of ours. You'll be responsible for managing guest communications from pre-arrival through post-departure, ensuring five-star service delivery and maintaining operational excellence behind the scenes. This role is key to guest satisfaction, retention, and positive review generation. Your Main Responsibilities: Key Responsibilities: Guest Services & Communication: (Primary Focus) Serve as the primary point of contact for guests across phone, email, OTA channels (Airbnb, VRBO), and messaging platforms Manage all communications across the entire guest journey: pre-arrival, in-stay, and post-departure Resolve complaints quickly and empathetically, protecting both guest satisfaction and company interests Proactively handle booking changes, cancellations, and special requests Monitor and respond to guest feedback, driving internal improvements in service delivery Ensure experiences that lead to positive reviews and repeat bookings Reservation & Revenue Management: Own the full reservation process: confirmations, modifications, cancellations Convert inquiries into bookings by following up on leads Match guests with ideal properties based on preferences and availability Coordinate early check-ins/late check-outs with housekeeping and field teams Back Office & Operational Support: Collaborate with cleaning crews, maintenance teams, and vendors to resolve guest issues Share guest communication with relevant departments for resolution Maintain accurate records of correspondence, bookings, and guest profiles Support basic admin functions: data entry, guest databases, vendor contact updates Ordering of supplies/consumables for Chicago units What We’re Looking For: Mandatory Reporting Requirements: You will be responsible for compiling and reporting on the following, on a weekly and monthly basis: Number of guest complaints handled Summary of complaints categorized into standardized buckets (e.g., cleanliness, check-in issues, noise, etc.) Financial impact and resolution summary (refunds, discounts, credits issued) Required Qualifications: Core Skills & Experience Native-level written and verbal English (5/5 on internal assessments) 2+ years in short-term rental guest services, reservations, or front office/hospitality roles High attention to detail and multitasking in fast-paced environments Self-motivated and comfortable working remotely with minimal supervision Strong problem-solving skills and customer-first mindset Technical Proficiency: Experience with PMS platforms (Guesty preferred, Track, or similar) Skilled with booking platforms like Airbnb, VRBO, Booking.com Proficiency in Microsoft Excel and Google Workspace tools Ability to quickly learn and adapt to new tools and workflows Preferred Qualifications: Direct experience using Guesty PMS Familiarity with vacation rental operations (short-term rentals) Exposure to basic financial tasks (e.g., issuing refunds, invoice tracking) Social media content creation skills for promotional guest messaging Availability & Flexibility: Must be available for shifts that support guests across multiple time zones (including evenings/weekends/holidays as needed) Occasional emergency response outside core working hours may be required Technical Requirements: Internet speed minimum 30mbps: Needs to be Wired (Buy a dongle if no LAN port) i5 11th Gen or higher Windows 11 / MacOS Catalina or higher Minimum of 8 GB RAM Private and quiet dedicated home office area (no roosters, dogs, children's noises in the background) Back-ups in case of power or internet provider interruptions Good headset and webcam (preferably noise-canceling headset) Why You’ll Love Working with Us: Competitive Salary — We offer a competitive salary that reflects the candidate’s experience, skills, and responsibilities. Remote Work — This role is 100% remote, allowing flexibility and eliminating daily commute. Paid Time Off — Standard leave entitlements (vacation, sick leave, vacation leave) for rest and well-being. HMO Coverage — Company-provided HMO plan, offering access to medical services via accredited hospitals and clinics under a Health Maintenance Organization. This helps ensure employees have access to routine checkups, consultations, and coverage for medical care. Apply To This Job