Vacation Rental Specialist with Streamline Experience

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. 

We are looking for a Vacation Rental Specialist for a Property management client of ours. This position is pivotal in providing outstanding customer service, managing reservations efficiently, and supporting back-office operations. The ideal candidate will excel in working independently, communicating effectively in a virtual setting, and ensuring a seamless experience for guests, property owners, and internal teams.

Key Responsibilities

Guest Services

• Serve as the primary contact for guests, delivering exceptional customer service.
• Respond to in-house guest emails, chats, and texts with professional and friendly written communication (e.g., lockbox, Wi-Fi troubleshooting, directions to homes, etc.).
• Answer in-house guest calls and assist with similar issues.
• Make outbound calls to incoming guests before arrival to ensure their needs are met.
• Respond to complaints or upset guests with professionalism and empathy, escalating when needed.
• Enter work orders for maintenance issues reported by guests.
  
  

Guest Reservation Management

• Communicate with potential guests via email, chat, text, and phone in a professional and friendly manner.
• Respond to emails with reservation information, confirmations, and additional details.
• Collaborate with guests to understand their needs, recommend properties, and answer questions regarding facilities and rates.
• Stay familiar with the area, company properties, and local attractions to answer inquiries.
• Advise guests on promotions or upgrades to enhance their experience.
• Manage OTA messaging (Airbnb, Vrbo, etc.).
• Handle the end-to-end reservation process: inquiries, bookings, alterations, and cancellations.
• Check voicemail and follow up with potential guests to convert leads.
• Manage sales leads through CRM/lead-tracking software.
• Process guest payments.
  
  

Guest Feedback Management

• Monitor and respond to guest reviews.
• Collect and analyze guest feedback to identify opportunities for improvement.
  
  

Back-Office & Accounting Support

• Streamline Expertise: Serve as the in-house specialist for the Streamline PMS, ensuring accurate use across reservations, listings, and financial operations.
• Bookkeeping & Accounting: Handle bookkeeping tasks directly within Streamline, including entering transactions, reconciling accounts, and managing year-end accounting processes.
• Check Processing & Banking: Coordinate with management and the office team to prepare checks within Streamline, process Visa charges, and ensure accurate payment tracking. (Checks will be printed in-office.)
• Assist property owners with inquiries.
• Process daily reservation and financial reports.
• Support office staff by coordinating with housekeeping, maintenance, and accounting as needed.
• Handle data entry for onboarding new properties into PMS and OTA listings.
• Maintain OTA system listings, including property photos, rates, and descriptions.
  
  

Foundational Requirements

• Excellent written and verbal English skills (phone, text, and email).
• Previous experience in guest services, reservations, or a related field.
• Proven experience with Streamline PMS (required).
• Strong bookkeeping and accounting knowledge, preferably within the vacation rental or hospitality industry.
• Strong organizational and multitasking abilities.
• Ability to work independently in a remote work environment.
• Attention to detail and a commitment to service excellence.
• Empathy, patience, and a customer-first mindset.
• Critical thinking and problem-solving skills.
• Ability to learn new software quickly.
• Willingness to ask questions when clarification is needed.
  
  

Schedule

• Primarily Monday through Friday.
• Flexibility to adjust based on business needs (two consecutive days off preferred).
  
  

Nice to Haves

• Vacation rental industry experience, especially with OTAs like Airbnb and Vrbo.
• Prior accounting experience in property management or hospitality.
• Experience in real estate or familiarity with real estate technology tools (e.g., ZipForms, FlexMLS, Dropbox, Google Workspace).
• Willingness to step in when the assistant is on holiday (assistant will also support with training).