Short Term Rental Property Assistant & Outreach

ABOUT US

We are a rapidly growing short-term rental company building long-term partnerships with property owners through our corporate leasing model. We pride ourselves on exceptional guest experiences, efficient operations, and using technology and AI to scale.

We're looking for a proactive, resourceful, tech-savvy Virtual Assistant who enjoys solving problems, talking to people, and taking full ownership of their work. This is a long-term role, and it's eligible to grow from part-time to full-time for the right person who does the job well.

SCHEDULE

Monday–Friday, 1:00–5:00 PM Eastern Standard Time (EST). Part-time to start, with a clear path to full-time based on performance.

HOW THIS ROLE WORKS — Priorities

This role has two sides, and the order matters:
1. Property management comes first. Guest communication, operations, scheduling, and platform support are always the top priority. These get handled promptly, every day.

2. Outreach fills the remaining time. When property management tasks are minimal or already handled, you'll shift to outbound calling and business development. It's the secondary responsibility — important, but never at the expense of guests and operations.

We're looking for someone who can read the day, take care of what's urgent first, and use the quieter stretches to drive outreach.

RESPONSIBILITIES

Primary — Property Management
1. Guest Communication: Respond promptly and professionally to guest inquiries before, during, and after their stay.
Resolve guest concerns while maintaining excellent service, escalating to the team when needed.

2. Operations & Scheduling: Coordinate cleaners, maintenance vendors, and tea ---------- mbers when operational issues arise.
Schedule appointments and keep tasks on track.
Watch operational workflows and flag potential issues before they become problems.

3. Airbnb & Platform Support: Communicate with Airbnb and other platforms on reservations, disputes, reimbursement claims, guest complaints, and policy questions.
Advocate professionally for the company to reach the best possible outcomes, staying calm through difficult conversations.

4. Technology & Systems: Use AI tools to work faster and smarter.
Learn new software quickly and keep records accurate in our property management system.

Secondary — Business Development & Outreach
(When property management responsibilities are light or already handled.)

1. Make outbound calls to property owners, real estate agents, and property managers.

2. Introduce our corporate leasing model and qualify properties for corporate leasing and/or short-term rental use.

3. Build rapport with prospects and confidently answer common questions about our business.

4. Accurately document each conversation and follow up with leads as needed.

QUALIFICATIONS

Required

• Excellent spoken and written English, with a clear, neutral accent for US phone calls.
• Strong customer service and communication skills.
• Highly organized and dependable, with the judgment to prioritize urgent property management tasks before outreach.
• Strong problem-solving skills and the ability to work independently.
• Tech-savvy and quick to learn new software.
• Hands-on experience using AI tools (ChatGPT, Claude or similar) to boost efficiency.
• Comfortable with outbound calling and handling objections and difficult conversations.
• A track record of efficient call sessions: in previous full-time outreach roles, you consistently made at least 100–200 calls per day. (This tells us you can run productive outreach in the time available — not a daily target for this role.)
• Reliable internet, a quality headset, and a quiet work environment.

Preferred

• Experience in short-term rental or hospitality.
• Experience using Airbnb.
• Experience with Hostaway property management software (strongly preferred).
• Experience with CRM and task-management tools.
• Background in sales, cold calling, customer support, or virtual assistance.

WHO THRIVES HERE

The person who does well in this role is a self-starter who doesn't wait to be told what to do, reads the day and prioritizes correctly, juggles multiple responsibilities calmly, communicates with confidence, and follows through until the job is done. You're detail-oriented, dependable, and genuinely enjoy learning new tools.

HOW TO APPLY

To show us you read the full post, please start your application with the codeword "GROWTH" and include:

A short note on your property management, guest-support, and outbound-calling experience.
Any short-term rental, Airbnb, or Hostaway experience you have.
A one- to two-minute voice recording introducing yourself, so we can hear your spoken English on the phone.

Applications that skip the codeword or the voice recording won't be reviewed. We read every application that follows these steps — we look forward to hearing from you!