AI Engineer, ResortPass

• We encourage candidates to apply even if they don't have 100% of the below qualifications. We believe in a holistic approach when evaluating talent for our team and post new roles often, so even if this role isn't quite right, we want to meet you!
• 5+ years of experience in software engineering, data engineering, or ML engineering, with meaningful exposure to at least two of these areas
• Hands-on experience building LLM-based applications or AI agents in production (not just notebooks) — including prompt design, tool use, orchestration, and evaluation
• Strong Python skills and experience with ML/AI tooling (e.g., LangChain, LlamaIndex, or similar orchestration frameworks; PyTorch or equivalent for model work)
• Solid data engineering fundamentals: building and maintaining ETL/ELT pipelines, working with data warehouses (e.g., Redshift) and data transformation tools like dbt
• Experience deploying ML models or AI systems into production backend services, ideally in a web application context
• Comfort working in or alongside a Ruby on Rails codebase — you don't need to be a Rails expert, but you should be able to integrate your work into an existing backend
• Strong SQL skills and an intuition for data modeling and data quality
• Demonstrated ability to work cross-functionally with product, engineering, and business stakeholders

Desirable

• ResortPass is looking for an AI Engineer to sit at the intersection of AI product development, data engineering, and ML infrastructure
• You'll be responsible for building and deploying AI agents that automate real guest and partner workflows, while also owning the ML infrastructure that makes those systems reliable, observable, and smart
• AI Concierge — A post-booking assistant that helps guests with day-of logistics, answers questions about their upcoming experience, and surfaces personalized upsell opportunities, all via SMS and chat
• Voice AI Booking Assistant — An AI agent that calls hotel spas and front desks to book appointments on behalf of guests, handling hold times, retry logic, and multi-turn conversations with hotel staff
• Conversational Search — A natural language search experience that helps guests discover the right hotel day pass based on what they're looking for ("a pool day near me with cabanas and cocktails"), rather than relying on filters alone
• You'll ship production AI systems that integrate directly into our Rails backend and interact with real guests, hotel partners, and third-party booking platforms
• You'll also build the real-time data pipelines and model-serving infrastructure that power our ML-driven marketplace — from search ranking to pricing to personalization
• We're looking for someone who can move fluidly between prompt engineering and pipeline engineering, someone equally comfortable designing an agent orchestration framework as they are debugging a dbt model or optimizing a Redshift query
• You'll work closely with our Product Engineering, Data, and Business teams to turn AI from a prototype into a core part of how ResortPass operates
• In your first 3–6 months, you'll ship production AI systems and build the infrastructure to support them:
• Design, build, and iterate on AI agents that handle complex, multi-step workflows — automated booking, guest communication via SMS and voice, and partner integrations — taking them from prototype to production
• Build and maintain the real-time and batch data infrastructure (pipelines, feature stores, model-serving layers) that supports our ML models and AI systems
• Develop evaluation and observability frameworks for AI agents — including logging, human-in-the-loop feedback loops, and quality metrics — so we can measure and improve agent performance over time
• Secondary focus: ML lifecycle & backend integration
• Integrate AI capabilities directly into our Ruby on Rails backend, working alongside backend engineers to ensure agents and models are deployed reliably within our existing architecture
• Own the full lifecycle of ML models in production: data collection, training, evaluation, deployment, monitoring, and iteration
• Collaborate with Product and Business teams to identify high-impact opportunities for AI and translate them into well-scoped technical projects
• Help shape ResortPass's AI strategy and technical roadmap as one of the earliest dedicated AI hires