Rethinking an organization in an Agile manner is a challenge that affects every organizational aspects and is surrounded by risks that must be appropriately managed. Beyond the used methodologies and frameworks, the goal is always to develop a mindset that allows the organization to " stand on their own feet" and embrace antifragility. In this talk we will describe a concrete transformation experience in a company working on the medical sector, with the operational office in Italy, and how it has been completely revolutionized. We will talk about successful changes and the less fortunate experiments, how the company developed its Way of Working (WoW) in agile manner, even going so far as to reorganize of the internal physical spaces. We will also take a look at how the aspects of the Program were developed: from the Portfolio to the Risk Management System, up to the revision of the Quality procedures.