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The literature on circular economy has highlighted the need for more studies focused on investigating the journey of individual companies in the transition toward sustainable processes. This paper addresses this need by focusing on the furniture design industry, showing how the transition requires the re-organization of knowledge regarding materials, processes, technologies, and product quality. This assumption is demonstrated through the design research activity conducted in 2019–2020 as the first part of broader research by Cassina LAB, a collaboration between Cassina Research and Development Centre and POLI.design of Politecnico di Milano. Based on the analysis of the Italian furniture industry between constraints and opportunities, the aim of the research is to identify critical issues and propose sustainable and circular solutions, tailor-made for Cassina. Through this example, the paper contributes to the literature in two ways. First, it adds to the understanding of how companies are adopting the circular economy paradigm. Secondly, it contributes to defining tools to implement new forms of knowledge of materials and re-design processes to deliver products that are compatible with a circular economy model.