< Speaker / Facilitator >
Cassiano Vailati
WeRoad, Freelance, Enterprise Software Consulting, Intelli
Connect in LinkedIn
Cassiano Vailati is Head of Technology at WeRoad, the group travel company, where he leads software and data engineering. He joined in 2018 and has scaled the team from 5 to more than 50 engineers, through startup and scale-up, working hand in hand with the product team.
His focus today is AI: the platforms WeRoad builds on, the AI products travellers use, and adoption across the company.
Before WeRoad, he was Lead Engineer at a software consultancy and has worked as a freelance software architect since 2017. He also founded and ran CremaWeb, a meetup community for web developers in his home town. He has been building software for close to 20 years, and remains passionate about new technologies, innovation and traveling.
COHOST with
Matteo Risso
Senior Product Manager
WeRoad
< About >
Everyone is experimenting with AI. Very few companies have turned it into the system they actually run on and even fewer are willing to show the messy middle.
Over the last two years WeRoad went from the first proof of concepts to an AI-native company, and this talk retraces that journey chapter by chapter, in the order it actually happened: the first AI products shipped to customers, AI-assisted engineering landing on every developer's desk, the company-wide rollout that put powerful tools in everyone's hands and the sprawl that came with it. That chaos is what led to the current chapter: a Company Brain that centralizes organizational knowledge, a data warehouse that gives AI real context, and a growing layer of automated processes and pipelines built on top.
For every chapter, Cassiano and Matteo share what was built and what was hard: learning curves, models that change under your feet, governance and trust at company scale. Matteo closes the loop from the product side, showing how this foundation transformed the way product managers work from prompting to shorten tasks to recurring agents embedded in the daily flow. The session ends with where the journey goes next and Q&A.
< Key learnings >
Start by shipping, not by strategizing - WeRoad's journey began with real AI products (support chatbot, search, translations, auto-documentation) and the unglamorous lessons that came with them: testing, verification, and new releases break things.
AI-assisted engineering compounds fast - What happened when agentic coding tools reached every engineer and PMs started opening pull requests: release cadence more than doubled in two years, with review overhead and cognitive overload as the real costs to manage.
Company-wide rollout creates sprawl before it creates value - When everyone can suddenly do everything, you get duplicated work, unverified answers, and a data team drowning in "but my numbers say otherwise". Governance isn't optional.
The Company Brain & Governance tools are the answer to the chaos - How WeRoad is moving from personal AI setups to a centralized brain: RAG over internal documentation and code, plus a data warehouse semantic layer that gives every AI interaction real organizational context.
A new operating model for product teams - How this foundation changed PM work end to end: from one-off prompts to recurring agents that update tasks after groomings, write issues, prototype on the design system, and open PRs.
< Tickets >
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