Quick Summary
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.
Qualifications
- 8+ years of software engineering experience, with at least 2 years operating at a Staff or equivalent level.
- Deep Python expertise: Highly proficient in writing production-grade Python services for this platform.
- Production experience with LLM-based systems: Built, shipped, and operated AI features or platforms at scale, understanding operational realities like prompt versioning, evaluation, cost management, observability, and failure modes.
- Strong architectural instincts: Design systems that start simple and evolve gracefully, knowing when to keep components in a single service and when to extract, and making pragmatic trade-offs between speed and extensibility.
- Familiarity with modern AI tooling ecosystem: Experience with frameworks and libraries such as PydanticAI, LangChain, LangGraph, LiteLLM, Langfuse, Phoenix, MLflow, or comparable tools, with the ability to evaluate and integrate them with confidence.
- Multi-agent architecture experience (strong plus): Designed systems with agent orchestration, tool calling, structured output, and context management.
- Comfort with a polyglot stack: Adaptability to read, understand, and integrate with Go services, PHP monolith, and React frontend, alongside the Python AI Platform.
- Infrastructure fluency: Comfortable with AWS, Kubernetes, CI/CD pipelines, and operating services in production.
- Cross-team influence: Proven ability to drive adoption of platforms, patterns, or standards beyond your immediate team through clarity and credibility.
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.