Guest Service Agent & Assistance

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. 

A. Guest Service Agent

• Respond to all guest messages within 5 minutes(goal: under 1 minute for simple responses), even without a full update
• Monitor all guest communication channels including Hostaway, Furnished Finder, email, texts, and phone calls
• Deliver clear, professional, and brand-aligned communication in every interaction
• Take immediate action on guest issues by creating and assigning Breezeway tasks
• Coordinate with internal team members to resolve all guest needs quickly and completely
• Proactively schedule mid-stay cleans and collect all associated fees
• Request, track, and confirm 100% of guest payments(mid-stay cleaning, pet fees, calendar hold fee, etc.), escalating when needed
• Accurately manage guest details and special requests to make parking permits and assist with other needs
• Adjust listing details, property intel pages, automated messages, and message templates as needed
• Maintain calendar availability and blocks in accordance with operational and sales needs as directed by Operational Manager and Leasing Manager
• Monitor and respond to guest reviews, and create follow up tasks for the operations team to address feedback
• Actively request positive reviews and take steps to prevent negative reviews when possible
• Reference and continuously update Notion (Property Intel Pages) to answer property specific questions and to improve response accuracy and efficiency
• Update Asana to keep property statuses and availability trackers and reservation checklists up to date
• Escalate urgent or high-risk issues to Operations Manager immediately

B. Leasing Assistant

• Working closely with the Leasing Manager to manage MTR reservations, including calendar blocking and unblocking based on guest move-out timelines and property readiness
• Monitor and respond to Furnished Finder inquiries and housing requests; escalate when needed
• Maintain and update the MTR reservation tracker and guest records throughout the booking lifecycle
• Send leases and addendums, and process reservation extensions while updating booking platforms accordingly
• Create direct reservations and ensure all required payments are completed
• Generate and manage lock codes for guests and vendors once requirements are met
• Coordinate background checks and assist with approvals as directed
• Schedule virtual tours and manage calendar coordination
• Complete guest handoff at check-in and direct guests to the guest service line
• Review notes and special conditions before approving bookings
• Support the Operations Manager with operational tasks as needed

C. Listing Assistant

• Analyze market data (occupancy, pricing, and revenue trends) to competitively price properties
• Adjust pricing and availability to maximize occupancy and revenue across all listings
• Create new property listings across platforms, ensuring accuracy, completeness, and strong presentation
• Maintain and update existing listings, including descriptions, photos, amenities, and pricing
• Optimize listings for visibility and performance (titles, descriptions, keywords, and platform-specific features)
• Track and report on occupancy and revenue performance across markets
• Maintain dashboards and internal reporting tools related to listing performance
• Ensure listings are published and active across all required platforms, including additional distribution channels and insurance portals
• Monitor listing quality and flag any issues that could impact bookings or guest experience
• Support leasing efforts as needed, including sending leases, background checks, or agreements

• Assist the Operations Manager with operational setup tasks such as utilities or platform-related updates

D. Finance Assistant

• Upload and organize all receipts into property-specific Dropbox folders on a weekly basis for every expense incurred that week
• Collect receipts from all sources, including WhatsApp threads, emails, utility websites, RingCentral texts, and online purchases
• Create internal receipts for:
  • Supplies transferred from bulk inventory to individual properties
  • Maintenance work completed by in-house technicians
• Track and allocate supply costs to the correct properties using inventory and transfer data (e.g., Sortly)
• Track and allocate in-house maintenance labor and materials to the correct properties using Breezeway and internal reports
• Pull and adjust reports to accurately calculate per-property charges for supplies used and in-house maintenance work
• Ensure all expenses are documented, categorized, and uploaded accurately and on time each week
• Upload trip and reservation information to document income-related receipts and revenue tracking
• Maintain clean, consistent, and audit-ready financial records across all properties

E. Marketing Assistant

• Assist with planning, creating, and scheduling social media content across platforms
• Respond to comments, messages, and engage with our audience in a timely, brand-aligned manner
• Support content organization, caption writing, and light research for posts and campaigns
• Coordinate with internal team members to gather content (photos, videos, updates)
• Maintain and update guest guidebooks, including recommendations and upsell opportunities
• Support email marketing efforts, including newsletters and promotional campaigns
• Monitor social media and marketing performance and flag opportunities for improvement
• Ensure consistency in brand voice, messaging, and presentation across all platforms
• Track and complete marketing-related tasks and projects in Asana
• Support the Operations Manager with marketing and operational tasks as needed

What We’re Looking For:

• Experience in hospitality, property management, or customer service
  • Experience communicating with guests and handling customer issues in real time

• Familiarity with digital tools used in property operations, including:
  • Breezeway
  • Asana
  • Notion
  • Hostaway (or other property management software)
  • Microsoft Office Suite (Outlook, Excel)
  • Social media platforms (Marketing Assistant role)

• Demonstrated professional traits aligned with a high-performance, guest-focused environment
  • Strong written communication and attention to detail
  • Ability to stay responsive and focused during all shifts, including low-activity periods
  • Ability to take ownership, follow through, and handle multiple tasks at once

This role is critical to our operation. Guests are our top priority, and the speed and quality of communication directly impact our reviews, revenue, and brand. We expect consistent, high-level performance in both guest communication and operational follow-through.

• All guest messages are responded to within 5 minutes (goal: under 1 minute for simple responses)
• Maintain a 5-star communication experience across all guest interactions
• 100% of guest fees are requested, tracked, and confirmed or escalated
• 100% accuracy in guest details, including parking permits and required information
• No missed messages, tasks, or incomplete follow-ups

We are looking for someone who takes ownership, stays attentive even during slow periods, and follows through on every detail. This role requires consistency, urgency, and pride in doing things the right way, as you are directly representing our brand to every guest.

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.