Associate AI Developer

About StaycationGo

StaycationGo is building technology and media tools for the short-term rental industry. Our platform helps vacation rental owners grow their bookings, manage guests, and optimize performance. We are part of the Staycation ecosystem, including the Destination Channel and the Staycation travel series.

We are a small but fast-moving startup team currently working with three developers to build the next generation platform for hosts.

Role Overview

We are looking for an AI Developer to build the conversational-AI layer of the StaycationGo platform and then help maintain and extend it alongside our current AI developer. The first project is a guest-facing chatbot (text and voice) that answers questions about a property and its stay.

The assistant is embedded in our guidebooks and property microsites and is grounded in real property data through retrieval-augmented generation (RAG), so answers are accurate to each specific listing rather than generic. After launch, you will continue working within the StaycationGo system on related AI and integration work.

Key Responsibilities

• Build and maintain a guest-facing chatbot for the guidebooks and property microsites, powered by Claude (or a comparable LLM).
• Implement a RAG pipeline that grounds answers in per-property and guidebook content, so responses are accurate to the specific stay.
• Add a voice interface using Claude or a managed voice service (e.g. Vapi, Retell, ElevenLabs), whichever is the pragmatic path.
• Integrate the assistant with StaycationGo's data and hooks: read property, guidebook, and booking data (PostgreSQL and the platform's existing APIs) so answers stay current.
• Design and install guardrails: scope answers to the property and stay, block off-topic or unsafe responses, prevent hallucinated facts and prompt injection, and fall back gracefully when confidence is low.
• Structure and maintain the content and embeddings the assistant retrieves from, keeping them in sync as property and guidebook data changes.
• Work in conjunction with the current AI developer on related AI and platform tasks after the chatbot ships.

Requirements

• Hands-on experience building LLM applications such as chatbots, RAG, or assistants, with Claude, OpenAI, or similar.
• Practical understanding of RAG: chunking, embeddings, vector search, and grounding answers in a source of truth.
• Comfortable integrating with APIs, databases, and webhooks, and able to wire an assistant to live application data.
• Experience with, or willingness to learn, a voice or conversational stack (Claude-native or a SaaS voice service).
• Working knowledge of prompt design and guardrails: scoping, safety, and injection resistance.
• Basic scripting or programming knowledge (TypeScript, JavaScript, or similar).
• Problem-solving mindset and ability to ship practical solutions quickly in a small startup environment.
• Preferred: hands-on experience with Strapi API, Docker, GitHub, PostgreSQL, and basic knowledge of SvelteKit (particularly how data flows).

What We Offer

- Monthly compensation of $750 USD.

- Flexible working hours and fully remote work.

- Opportunity to learn and grow within a startup environment.

- Future potential for additional benefits such as health coverage.

- Opportunity to help build technology used by hosts and the travel industry worldwide.