About WeRoad: connecting people, cultures, and storiesFounded in 2017, WeRoad is a fast-growing startup that is disrupting the travel industry in Italy, Spain, UK, Germany, France, Switzerland and… the USAWith 200 team members and 4K Travel Coordinators, we're a community of travelers who turn every trip into a life-changing experience. We connect like-minded millennials and send them on adventures to 1000+ destinations worldwide.
We're on a mission to design and deliver experiences worth living and sharing, through rewriting the rules of the travel industry.
Sounds exciting? Before you apply, please read through our Cultural Manifesto

About the role
JOB TITLE: AI Product EngineerLOCATION: Full remote or Hybrid (Milan)TYPE OF CONTRACT: Full-Time PermanentSALARY RANGE: up to 55KYou'll join the Science Team, the team that owns everything AI at WeRoad: from the conversational assistant that talks to travelers across five European markets, to AI-powered search, personalisation algorithms, content and internal tools. It's a small, hands-on team where your code ships to production and real users from the first weeks. We're looking for someone sharp, fast and hungry. That matters more than seniority.

What you'll do
Build, ship and maintain LLM-powered features in production – agents, classifiers, RAG pipelines and AI search used by thousands of travelers every dayDesign and iterate on LangGraph workflows, prompts and tool-calling logic, turning business needs into reliable AI behaviorSet up and run evaluations: define test sets, track quality, latency and cost with tracing/observability tools (e.g. Langfuse), and use the data to decide what to improveIntegrate AI services with WeRoad's product and data stack (APIs, databases, BigQuery, cloud infrastructure on GCP)Optimize what's already live: token usage, model routing,



prompt efficiency and response qualityWork closely with Product, Customer Care, Marketing and Data to spot new AI use cases and take them from prototype to productionOwn problems end-to-end: from understanding the need to shipping and monitoring the solutionWhat we're looking forProduct sense – you start from the problem, not the model. You ask who it's for and what changes for them, and you know when not to use AIExperience as a software engineer and/or product engineer, ideally in a product company or a fast growing startupAgency and ownership – you don't wait for a perfect ticket. You take something vague, make it concrete, ship it and own what happens afterEngineering skills – you understand what it takes to run AI in production. Asked to ship agents serving 100k queries a month, you can reason about the system-level trade-offs: latency, cost, reliability, scalability.
Experience using TypeScript or Python is a strong plusYou've built things with AI – at work, in research or on your own. We care about what you built and whyYou measure before you trust – a prompt or a model isn't done until you've checked how it behavesClarity – You can explain technical choices to non-technical peopleFluency in EnglishYou will love working at WeRoad ifYou dream big, aim higher, and push yourself beyond limits you didn't think possible. Challenges excite you, and you're hungry for the next win.
You want to be part of a young, smart,



and fun team that shares your passion for travel. You thrive in a community of bold thinkers and doers who challenge and inspire each other.
You're an entrepreneur at heart, take responsibility from day one, and move fast to make things happen.
You prefer adventure over routine and embrace the fast-paced, ever-changing ride of a scaleup. You make decisions quickly, test, learn, and adapt—because growth comes from action.
You believe in the power of people. Our WeRoaders and Travel Coordinators are at the core of everything we do, and you're eager to be part of something bigger.
BenefitsPerformance-based bonus – A discretionary annual variable premio, based on performance and company results.
A free WeRoad trip every year – Choose your dream destination with 1,400/year travel discount or travel even more as a Travel Coordinator.
Trust-based holidays – We believe performance is driven by impact, not by hours at a desk. You are encouraged to take the time you need to recharge, beyond contractual minimums, within shared guidelines.
Opportunities to learn – We invest in your growth with training and learning opportunities.
New parent support – 3,600/year for 3 years after birth or adoption (or prorated if your child is under 3 when you start at WeRoad).
Extra benefits – Meal vouchers (8/day – when applicable), a 1,000 bonus for your wedding or civil union, and one-off bonus when you hit 5 years with us.
Fun – A vibrant co-working space, team buildings and meet-ups.
Hybrid working – Flexible working, and we support you to work from your destination of choice up to 1 month per year.
Selection processAt WeRoad, cultural fit matters as much as skills. We assess both the what, what someone brings and the how,

📌 AI Product Engineer (Milano)
🏢 Weroad
📍 Milano