Job Description
Description
NOTE: This is a FULLY remote role, but the candidate must be within EMEA to collaborate with their team, peers, and internal customers. You do not have to be in the specific country or city shown in this listing, but please only apply if you are physically based within EMEA.
Trusted by 20,000+ property managers worldwide, Hostaway is an industry leading, AI-powered vacation rental management platform designed for professional short-term rental operators. Hostaway brings everything together for greater efficiency and faster growth.
Profitable, high-growth, and the first short-term rental Property Management System unicorn 🦄. Join us at our most exciting stage yet! Learn more about our recent valuation and story here.
About the role
We’re building Hostaway’s AI Platform - the foundational infrastructure that will power every AI-driven feature across our product. This is not a feature team bolting AI onto existing workflows. It’s a platform team building the agentic framework that enables every engineering team at Hostaway to ship reliable, production-grade AI capabilities.
As a Staff Engineer, you’ll own the architecture and technical direction of this platform. You’ll lead the design and implementation of a multi-agent system that includes an agent orchestrator, LLM gateway, prompt and tool versioning, evaluation framework, and end-to-end observability. Your work will directly determine how effectively Hostaway can deliver AI-powered experiences to over 50,000 property managers and their guests.
This is a high-autonomy, high-impact role. You’ll report directly to engineering leadership and collaborate closely with product, design, and engineering teams across the company. You’ll inherit a well-defined architecture and a strong technical foundation - your job is to take ownership, evolve it, and scale it as the platform matures and adoption grows.
What you’ll do:
Own the AI Platform architecture, lead the technical vision for the multi-agent system - agent delegator, sub-agents, config service, LLM gateway, evaluation framework, conversation history, and observability stack.
Build production-grade AI infrastructure, design and implement the core services that make AI features reliable, versioned, observable, and safe to ship at scale.
Drive the evaluation and quality story, establish quality gates, prompt comparison workflows, hallucination detection, and CI/CD integration so that every AI feature ships with measurable confidence.
Shape the LLM gateway strategy, ensure provider failover, model routing, cost tracking, and rate limiting are handled centrally - eliminating duplicated effort across teams.
Champion cross-team adoption, work with product teams across Hostaway to make the AI Platform easy to adopt. Publish internal blueprints, define integration patterns, and ensure teams can build specialized agents without deep platform knowledge.
Influence engineering-wide practices, drive best practices for prompt engineering, tool design, observability, and agent testing across the organization.
Mentor and elevate engineers, raise the technical bar across the AI team and beyond - through code review, architectural guidance, and hands-on pairing.
Requirements
8+ years of software engineering experience, with at least 2 years operating at a Staff or equivalent level.
Deep Python expertise. This platform is built in Python - you should be highly proficient and opinionated about writing production-grade Python services.
Production experience with LLM-based systems. You’ve built, shipped, and operated AI features or platforms that serve real users at scale. You understand the operational realities: prompt versioning, evaluation, cost management, observability, and failure modes.
Strong architectural instincts. You can design systems that start simple and evolve gracefully. You know when to keep components in a single service and when to extract. You make pragmatic trade-offs between speed and extensibility.
Familiarity with the modern AI tooling ecosystem. Experience with frameworks and libraries such as PydanticAI, LangChain, LangGraph, LiteLLM, Langfuse, Phoenix, MLflow, or comparable tools. You don’t need to know all of them, but you should be able to evaluate and integrate them with confidence.
Multi-agent architecture experience is a strong plus. If you’ve designed systems with agent orchestration, tool calling, structured output, and context management, you’ll hit the ground running.
Comfort working across a polyglot stack. The AI Platform is Python, but it doesn’t exist in isolation. Hostaway’s product includes Go services (including existing MCP servers), a PHP monolith, and a React frontend. You don’t need to be proficient in all of these, but you should have the curiosity and adaptability to read, understand, and integrate with code across these technologies.
Infrastructure fluency. Comfortable with AWS, Kubernetes, CI/CD pipelines, and operating services in production.
Cross-team influence. You lead through clarity and credibility, not authority. You’ve successfully driven adoption of platforms, patterns, or standards beyond your immediate team.
What Success Looks Like:
The AI Platform is the trusted foundation for every AI feature at Hostaway - teams build on it by default, not by exception.
Prompt changes are versioned, tested, and rolled out with the same rigor as code deploys.
AI features in production are observable, cost-tracked, and recoverable - when something breaks, the team knows within minutes, not days.
Other engineering teams actively seek your guidance on building AI capabilities - you’re the go-to technical authority for applied AI at Hostaway.
The platform scales from the current set of use cases to a broader agent ecosystem without requiring fundamental rearchitecture.
