The Digital impacts our daily lives and Digital Transformation will impact the global future. Artificial Intelligence (AI) represents one of the most promising technologies for the future. However, there is a clear difficulty for the companies to use AI and also to adopt methodologies, tools and emerging technologies. This article describes the transformation of the automatic process of reading and forwarding financial documents of Aveleda, a viticulture organization. The goal was, through innovative approaches based on AI, to improve a system that was becoming more and more ineffective. The approach used was to modernize the OCR system, that was already being used, and act on distribution mechanisms to improve the process’ efficiency. Resourcing to new developing approaches and tools, not only a solution was achieved, but also relevant contributions on several knowledge dimensions.