Experienced Short-Term Rental (STR) Virtual Assistant

About Us: Hilltop Ventures operates at the intersection of hospitality and real estate, managing short-term and mid-term vacation rentals and traveling nurse housing. We move fast, prioritize exceptional guest experiences, and operate a revenue-focused culture. We are expanding our team and looking for 3 Full-Time Virtual Assistants to take ownership of our daily operations starting mid-July. Who We Are Looking For: We are seeking a highly organized administrative powerhouse with a strong background in Customer Service, Executive Assistance, or Clerical support. While we are open to diverse backgrounds, prior experience working in short-term rentals (STR) or supporting upper-level management is highly preferred. We operate with a strict zero hand-holding policy. We will provide thorough onboarding on our specific software platforms, but we require independent critical thinkers who can accurately assess a situation, manage client expectations quickly, and resolve issues without needing permission for every small step. Core Requirements: 1. Experience: Minimum of 2 years of professional experience in Customer Service, Executive Assistant, or Clerical/Admin roles. (Experience in vacation rentals or executive-level support is a major plus). 2. Mindset: Highly organized, proactive, and a natural critical thinker. You notice problems before they happen and solve them independently. 3. Speed & Independence: Capable of handling fast-paced customer expectations quickly and decisively. 4. Communication: Fluent, highly professional written and spoken English. 5. References: Professional references are strictly required and will be verified before hiring. 6. Availability: Ready to start mid-to-late July. This is a full-time role (up to 45 hours/week) with shift-based coverage, including a 30-minute shift overlap window. 7. Technical Reliability: Stable high-speed internet connection and a reliable backup power solution. Key Responsibilities: 1. Guest Relations: Manage guest communications across Airbnb, VRBO, and direct booking channels. Respond quickly and professionally to inquiries, check-in questions, and mid-stay requests. 2. Conflict Resolution: Use critical thinking to de-escalate issues, handle guest complaints, and manage expectations quickly and smoothly to protect our 5-star review status. 3. Team Coordination: Coordinate with our cleaning and maintenance teams (using tools like Turno) to ensure properties are perfect for arrival. 4. Administrative & Claims Support: Handle basic data entry, track leads for mid-term rentals, and file platform reimbursement claims for property damages. What We Offer: 1. Hourly Rate: $5.00 – $8.00 / hour (commensurate with experience). 2. Revenue Bonuses (Uncapped): Direct commissions and bounties for guest upsells, property referrals, and successfully processed damage claims. "13 month bonus" opportunity year around. Tools We Use (We Will Train You): Hostaway, Turno, Airbnb, VRBO, and standard administrative tools. How to Apply: To prove you possess the attention to detail and critical thinking skills we are looking for, please reply with the phase: 1. A brief summary of your experience (minimum 2 years required), highlighting any STR or upper-management support background. 2. Contact information for at least two professional references (or a statement confirming they are ready to be provided immediately upon request). 3. An example of a time you had to solve a difficult customer or operational problem independently without asking a supervisor for help. 4. End your proposal with the exact phrase "I am ladybug. Spot on!" so we know you read this entire posting. Applications without this phrase will be automatically declined.