Virtual Assistant / Software Developer

Company: Second Home Rentals LLC
Location: Remote
Job Type: Contract / Project-Based (with potential for ongoing work)

About Us

Second Home Rentals LLC is a growing short-term rental business managing multiple Airbnb units. We’re looking for a tech-savvy Virtual Assistant with software development/automation skills to build an AI-powered system that streamlines guest communications, fee collection, claims processing, and team coordination.

This role is ideal for someone who has experience with AI agents, workflow automation, APIs (Hospitable, Airbnb, spreadsheets), and property management tools.

Responsibilities

You’ll be responsible for designing and building a software/AI agent that automates our Airbnb operations step by step:

AI Guest Communication

Build an AI agent that integrates with Hospitable to handle guest messaging.

Manage guest inquiries, check-in/check-out communications, and common FAQs.

Extra Services & Fee Management

Send resolution requests for parking, early check-ins, late check-outs, etc.

Track all extra service payments in an Excel/Google Sheet for easy review.

Follow up with guests who haven’t paid before check-in.

AirCover Claims Support

Collect documentation from guests for any property damages.

Submit AirCover claims on Airbnb with the necessary evidence.

Guest Review Management

Understand the quality of stay from guest communication and experiences.

Draft and submit reviews for guests after checkout.

Cleaner Coordination

Send automated reminders to cleaners one day before scheduled cleans.

Project Stages

The build will be done in phases:

Stage 1: AI Guest Communication
Stage 2: Cleaning Team Reminders
Stage 3: Resolution Requests & Fee Tracking
Stage 4: AirCover Claims Automation

Requirements

Proven experience with automation tools (Zapier, Integromat/Make, n8n, etc.) or custom-coded solutions.

Experience with AI agents / chatbots (OpenAI, LangChain, Rasa, or similar).

Ability to integrate APIs (Hospitable, Airbnb, Google Sheets, etc.).

Strong organizational and problem-solving skills.

Familiarity with Airbnb hosting workflows is a big plus.

Reliable, detail-oriented, and proactive.

What We Offer

Flexible, remote work environment.

Competitive project-based pay.

Opportunity to expand into a long-term automation role as the business grows.

Work directly with a fast-scaling Airbnb business and shape the future of our AI-driven property management system.

How to Apply

If you’re interested, please send:

A short introduction about your background.

Examples of automation/AI projects you’ve built.

Your proposed timeline & hourly/project rate for Stage 1 (Guest Communication).