Operations Assistant

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 Operations Assistant for a Property management company client of ours. This role is crucial in supporting the CEO and Operations Manager by taking ownership of key operational and administrative tasks, ensuring efficiency, accuracy, and ultimately, contributing to our mission of delivering unreasonable hospitality. The ideal candidate thrives in a fast-paced environment, easily moves between working independently and as a team, possesses exceptional communication & critical thinking skills, and has a keen eye for detail.

Responsibilities:

I. Air Traffic Control & Communication Hub:

● Centralized Communication Management:

○ Proactively monitor and manage all incoming communications across email, phone, and designated platforms (Conduit, Slack, Gmail).
○ Categorize, prioritize, and respond to guest & owner messages promptly and professionally. Elevate complex issues to the Operations Manager as needed.
○ Maintain a "zero inbox" policy in Conduit/Gmail by processing, delegating, and archiving communications daily. Ensure all relevant information from these channels is captured and updated in relevant databases.
○ Become a power user of Conduit, Slack, Gusty and Breezeway, utilizing their full functionality for efficient communication and task management.

● Task Creation & Delegation:

○ Translate guest inquiries, maintenance reports, housekeeping notes, and internal communications into actionable tasks for appropriate team members within Slack and Breezeway.
○ Clearly define task requirements, deadlines, and relevant property/guest information.

● Follow-Up & Quality Assurance (Internal):

○ Systematically follow up on all delegated tasks to ensure completion within established timelines.
○ Verify resolution and quality of work performed by team members (e.g., confirm maintenance issues are truly resolved, housekeeping tasks are completed to standard.
○ Provide constructive feedback to team members and management regarding task completion and adherence to standards.

● Guest Satisfaction & Proactive Outreach:

○ Implement a structured follow-up process for guests post-checkout to gather feedback and ensure satisfaction.
○ Identify opportunities for proactive guest communication (e.g., pre-arrival welcome messages, mid-stay check-ins for longer stays, weather alerts, local event recommendations).

II. Data Integrity & System Management:

● Database Management:

○ Rigorously maintain and update all operational databases and master sheets (e.g., property master sheet, guest database, vendor contact list).
○ Specifically, action updates based on team communications (e.g., if a master code or garage code is changed in Slack, immediately update the master sheet and relevant guest communications).
○ Ensure consistency of information across all platforms (e.g., listing sites, internal databases, property management software).

● Listing & Distribution Quality Assurance:

○ Conduct regular audits of all property listings across various distribution channels (Airbnb, VRBO, direct booking site) to ensure 100% accuracy of data, pricing, descriptions, and imagery.
○ Verify that amenities listed are truly present and functioning.
○ Update or verify notes on listings based on guest feedback (e.g., if a guest reports a missing amenity, confirm its absence/presence and update the listing accordingly or create a task for procurement).
○ Proactively identify and resolve any "random calendar blocks" or discrepancies that could impact bookability.

● Visual Asset Management (Photos & Content):

○ Regularly review property photos across all listings. Are they up-to-date, high-quality, and representative of the current property condition?
○ Monitor seasonality in photos. If not current (e.g., winter photos in summer), create tasks for Ashley & Jon to update.
○ If no appropriate seasonal photos exist, coordinate with Ashley & Jon to schedule new photoshoots.
○ Ensure all listings consistently adhere to Company's style guide and branding.
○ Verify that all listings include the Company snippet at the beginning of the description.
○ Confirm accurate and clear parking information is present on all listings.
○ Verify distance information to key attractions/landmarks.
○ Ensure a drone/location shot is present in the picture gallery of each listing.
○ Check for clear, concise bullet point summaries of property features.

III. Performance Tracking & Reporting:

● Guest Feedback Loop:

○ Establish and manage a system to track the number of guest requests and complaints from initiation to full resolution.
○ Categorize issues (e.g., housekeeping, maintenance, general inquiry) to identify trends and areas for improvement.
○ Provide regular reports on request/complaint volume, resolution times, and recurring issues.

● Marketing & Data Enrichment:

○ Extract email addresses from guest communications (with appropriate opt-in if required) and add them to Company's marketing list for future promotions and newsletters.
○ Collaborate with marketing to track and report on the performance of listing photos (which photos correlate to higher bookings/engagement) and headlines.

IV. Daily Operational Oversight:

● Financial & Booking Integrity:

○ Daily verification that all guest payments are up to date and reconcile with booking records. Flag any outstanding payments immediately.
○ Cross-reference Breezeway with property management software to ensure homes marked "clean" in Breezeway accurately reflect their status for booking availability.
○ Proactively check that no homes are inadvertently blocked for booking due to outdated cleaning or maintenance statuses. Ensure Instant Book (IB) settings are correct based on property readiness.

● Check-in/Check-out Management:
○ Confirm that all upcoming check-ins for the day have successfully completed the verification process in SuiteOp. Address any pending verifications.
○ Review all check-outs for the day, noting any special instructions (e.g., late check-outs, specific guest requests, potential issues from the stay).

Detailed Task List:

I. Air Traffic Control

● Monitor Email/Phone/Conduit (Ongoing, multiple times daily):

○ Categorize incoming messages (guest inquiry, reservation change, maintenance report, housekeeping report, owner communication, vendor inquiry, marketing, spam).
○ Prioritize messages based on urgency (e.g., active guest issues, immediate booking inquiries, urgent maintenance).
○ Flag or label messages requiring specific action or follow-up.
○ Archive or delete irrelevant messages.

● Respond to Guest Messages and Reviews (Ongoing, within service level agreements):

○ Draft personalized and professional responses to guest inquiries (pre-booking questions, during-stay issues, post-stay feedback).
○ Address all feedback from reviews (positive and negative) promptly and thoughtfully.
○ Escalate complex or sensitive guest issues to CEO for guidance.
○ Maintain a library of templated responses for common inquiries, customizing each for a personal touch.

● Communicate/Create Tasks (Slack/Breezeway) for Team Members (Ongoing):

○ Housekeeping Tasks: Create tasks for cleans, mid-stay refreshes, linen changes, amenity restocking requests.
■ Detail: Include property name, unit, guest name (if relevant), specific instructions, date/time needed, and any photos or relevant context.
○ Maintenance Tasks: Log issues reported by guests or team (e.g., leaky faucet, broken appliance, Wi-Fi issues).
■ Detail: Include property, exact location of issue, description of problem, guest impact, urgency, photos/videos if available, instructions for access.
○ Concierge/Guest Experience Tasks: Special requests (e.g., arranging a specific tour, dinner reservation, pre-stocking groceries).
■ Detail: Guest name, property, request details, budget, timeline, preferred vendors.
○ Supply Chain/Inventory Tasks: Notifying the Company about of low stock on amenities, cleaning supplies.
○ General Administrative Tasks: As assigned by the CEO.

● Follow Up and Ensure Everything is Done (Daily/Ongoing):

○ Review open tasks in Slack/Breezeway.
○ Ping team members for updates on overdue or pending tasks.
○ Confirm task completion and verify quality (e.g., cross-check photos from housekeeping, confirm guest reported issue is resolved).
○ Update guest or owner on resolution status.

● Follow Up with Guests and Ensure They are Satisfied (Post-Stay/Proactive):

○ Automate (if possible, or manually schedule) post-checkout satisfaction surveys/messages.
○ Review survey responses and address any outstanding concerns.
○ Reach out to guests with specific issues during their stay to ensure full satisfaction after resolution.
○ For long-term guests, schedule mid-stay check-ins.

● Ensure Databases are Up to Date Based on Team Communications (Daily):

○ Master Property Sheet: Update master codes, garage codes, alarm codes, Wi-Fi passwords, vendor notes, specific property quirks, guest access instructions, etc., as communicated by maintenance or other staff.
○ Guest Database (CRM): Add new guest contact info (if applicable and opt-in obtained), note preferences, previous issues, special requests, VIP status.
○ Vendor Contact List: Update contact details, service notes, preferred vendors, pricing changes.
○ Emergency Contact List: Verify all emergency contacts for properties are current.

● Train Conduit - Ensure all Inboxes are at Zero (Daily - End of Day Ritual):

○ Process every message: Respond, delegate, or archive.
○ Utilize Conduit's tagging/labeling system for efficient organization.
○ Identify recurring themes or questions to suggest new automation rules or templates.

II. QA (Quality Assurance)

● Review Listings/Distribution and Ensure Data is Correct (Weekly/Bi-Weekly Audit):

○ Compare direct booking site listings with OTA (Airbnb, VRBO) listings.
○ Check pricing accuracy against rate management tools/strategies.
○ Verify property descriptions, amenity lists, bedroom/bathroom counts.
○ Ensure policies (cancellation, house rules) are consistent.
○ Look for any broken links or display errors.

● Update or Verify Notes on Listings if Guest Feedback Leads to Adjustments (Ongoing):

○ If a guest notes a missing amenity, verify its absence/presence. If truly missing, create a task for procurement/Ashley and update the listing description.
○ If a detail is incorrect (e.g., "hot tub available" but it's currently out of order), update the listing and flag for maintenance/repair.
○ If a guest gives positive feedback on a specific feature, highlight that in the listing.

● Ensure there are No Random Calendar Blocks (Daily/Weekly Spot Check):

○ Review the master booking calendar for any unintentional blocks or discrepancies that would prevent bookings.
○ Investigate the source of any unexplained blocks (e.g., system error, manual input error).
○ Work with Ashley to resolve any booking conflicts.

● Are Pics Updated? (Monthly/Quarterly Audit & Event-Driven):

○ Linens: Confirm photos show appropriate linens for the season.
○ Season: Are photos seasonally appropriate (e.g., no heavy snow in summer listings unless emphasizing year-round appeal)?
■ If not, create a task for Ashley & Jon to update/re-shoot.
■ If no current photos exist for the season, prioritize new photography.
○ Do all listings:
■ Match style? (Consistent branding, lighting, professional look).
■ Have Elysian snippet at the beginning? (Branded introduction).
■ Have parking info? (Clear, accurate details on parking availability and restrictions).
■ Have distance info? (Distance to major attractions, ski resorts, town center, etc.).
■ Have Drone/location shot in pics? (Showcases the property's setting and surrounding beauty).
■ Have bullet point summaries? (Easy-to-read highlights of key features).
■ Proactive Note: Suggest new photo opportunities based on seasonal changes, new amenities, or local events.

III. Tracking

● Track # of Guest Request/Complaints Until They are Closed (Daily/Weekly Reporting):

○ Utilize Breezeway or a dedicated spreadsheet/CRM to log every guest request/complaint.
○ Assign categories (housekeeping, maintenance, noise, booking issue, etc.).
○ Track key metrics: Date reported, date assigned, date resolved, resolution details, responsible team member, guest satisfaction with resolution.
○ Generate reports for Ashley and CEO to identify trends, pain points, and areas for operational improvement.

● Emails Shared with Us - Add to Marketing List (Ongoing):

○ Identify emails from guest inquiries, direct bookings, or interactions where explicit/implied consent for marketing communications is present.
○ Manually or use automation to add these to the marketing CRM/email list.
○ Ensure compliance with privacy regulations (GDPR, CAN-SPAM).

● What Photos Perform the Best (Bookings) (Quarterly Review with Marketing):

○ Work with marketing to analyze listing performance data.
○ Identify which lead photos and internal gallery photos correlate with higher click-through rates, inquiries, and bookings.
○ Suggest A/B testing for photos on listing sites.

● What Headlines Perform the Best (Bookings) (Quarterly Review with Marketing):

○ Analyze listing headline performance for similar metrics.
○ Suggest variations for headlines to optimize conversion.

IV. Daily

● Ensure all Guest Payments are Up to Date (Morning Check):

○ Review upcoming arrivals and ensure all payments have been processed and confirmed.
○ Flag any failed payments or outstanding balances immediately and initiate follow-up procedures (automated reminders, direct communication).

● Ensure Homes Marked "Clean" in Breezeway Match with Master Booking System (Morning Check):

○ Cross-reference cleaning statuses in Breezeway with the booking system's availability.
○ Identify and resolve any discrepancies to prevent overbookings or unnecessary blocking.
○ Ensure cleaning teams are accurately updating statuses.

● Ensure no Homes that Should Not Be Bookable Due to Not Being Clean or Maintenance Issues are Blocked - IB On/Off (Morning Check):

○ Verify that properties requiring cleaning or maintenance are correctly blocked for Instant Book (IB Off) or otherwise unavailable.
○ Conversely, ensure properties that are clean and ready are immediately available (IB On).
○ This is crucial for preventing negative guest experiences due to unready properties.

● Ensure all Check-ins Have Gone Through Verification Process in SuiteOp (Morning Check):

○ Review SuiteOp for pending guest verifications for same-day and next-day arrivals.
○ Follow up with guests who haven't completed verification.
○ Notify Company/CEO of any guests who are unable to complete verification or pose a potential risk.

● Checkouts of the Day - Special Notes: Late Check Out (Morning Check):
○ Review all properties checking out on the current day.
○ Note any approved late check-outs and communicate these to the housekeeping team.
○ Identify any specific instructions for check-outs (e.g., early departures, known issues with property).
○ Prepare for post-checkout communications.

Skills and Qualifications:

● Exceptional Organizational Skills: Ability to manage multiple tasks, deadlines, and information streams simultaneously.
● Meticulous Attention to Detail: A "nothing falls through the cracks" mindset.
● Proactive & Problem-Solving: Ability to anticipate needs, identify potential issues, and suggest solutions before they escalate.
● Strong Communication Skills (Written & Verbal): Clear, concise, professional, and empathetic communication.
● Tech Savvy: Proficient with communication platforms (Slack, email), property management software (Conduit, Breezeway, SuiteOp), CRM systems, Google Workspace (Sheets, Docs), and comfortable learning new tools quickly.
● Independent & Self-Motivated: Ability to work effectively with minimal supervision.
● Hospitality Mindset: Understanding of guest needs and a genuine desire to provide excellent service.
● Time Zone Flexibility: Ability to work within or overlap with Company's operational hours.
● Experience: Previous experience in hospitality, property management, or a virtual assistant role is highly desirable.