AI Engineer

About WeRoad: connecting people, cultures, and stories

Founded in 2017, WeRoad is a fast-growing startup that is disrupting the travel industry in Italy, Spain, UK, Germany, France, Switzerland and… the USA!

With 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 Engineer

LOCATION: Full remote or Hybrid (Milan)

TYPE OF CONTRACT: Full-Time Permanent

SALARY RANGE: up to 55K

You'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 day

• Design and iterate on LangGraph workflows, prompts and tool-calling logic, turning business needs into reliable AI behavior

• Set 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 improve

• Integrate 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 quality

• Work closely with Product, Customer Care, Marketing and Data to spot new AI use cases and take them from prototype to production

• Own problems end-to-end: from understanding the need to shipping and monitoring the solution

What we're looking for

• Product 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 AI

• Agency and ownership – you don't wait for a perfect ticket. You take something vague, make it concrete, ship it and own what happens after

• Engineering 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. Whether you learned this at university or in industry doesn't matter; the language doesn't either (TypeScript or Python is a plus)

• You've built things with AI – at work, in research or on your own. We care about what you built and why, not your years of experience or the frameworks on your CV

• You measure before you trust – a prompt or a model isn't done until you've checked how it behaves

• Clarity – You can explain technical choices to non-technical people

• Fluency in English

You will love working at WeRoad if

• You 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.

Benefits

• Performance-based bonus – A discretionary annual variable bonus, 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 process

At WeRoad, cultural fit matters as much as skills. We assess both the what, what someone brings and the how, how they work and live our values. With multiple steps, we make sure every new joiner is not just a match, but 150% aligned with our Culture.

The selection process will consist of:

1. Application: show us what you built.

2. Introductory call with Talent Acquisition Lead

3. Technical and background-based interview with Hiring Manager

4. Case Study / Second technical interview

5. Culture Champions step

WeRoad is an equal opportunity employer: we consider for employment all applicants, regardless of their race, religion, color, ancestry, national origin, sex, sexual orientation, gender, gender identity, age, family status, political affiliation, disability, and any other legally protected characteristic.

Statistically speaking, women are less likely to apply for roles where they don't fit the job description perfectly. Don't let a checklist hold you back: if you're passionate about the role we encourage you to apply with enthusiasm!