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Digital transformation is one of the biggest phenomena of this decade. One enabler of this revolution was cloud computing. Today, software engineers can deliver software as a service (SaaS), which is accessible to users through the Internet. Slack, Shopify, and Dropbox are examples of successful SaaS. We are experiencing an emergence of numerous small web applications with easy-to-use features for specific domains such as project management, accounting, resources management, customer relationships, and so forth. Thus, SaaS has been recognised as particularly well suited for the digital journey of small enterprises. However, surveys conducted by governmental agencies reveal a low adoption rate of SaaS by small enterprises in traditional sectors such as construction, services, and dealership. Previous studies have highlighted a lack of top management support, a weak relative advantage perceived, and a lack of knowledge as the key reasons for this low level of adoption. Whilst academic research defines these critical factors, it has not found potential solutions to mitigate them. Thus, this thesis presents two exploratory studies to enhance the adoption of digital practices by small traditional enterprises (STEs). A first study explored the value of leading collaborative projects between students and STEs about the assessment of SaaS solutions. A secondary objective of this initiative was the design of a platform acting as an open innovation platform. A three-year study allowed the completion of thirty-nine projects and the testing of two different platform designs. The feedback from students demonstrated the value of a well-structured platform composed of different management models for each project phase. Furthermore, 67 per cent of the STEs involved on the platform acknowledged the value of such collaborative projects. However, the collaborations did not improve top management support, and projects tended to stagnate because of various organisational factors. A second study, using a mixed-methods research design, was performed to explore the relations amongst the organisational factors acting as enablers and barriers to the digitalisation of STEs. The objective was to improve understanding of TSEs' situation and devise a proposition to enhance top management support. An academic contribution of this study was the design and application of a conceptual framework combining organisational factors from the literature on dynamic capabilities, organisational inertia, and intellectual capital. The combination of the qualitative observations and quantitative results highlighted the importance of the sensing and leadership capabilities for STE directors. They also revealed the mediator effect of the relational capability on the development of these latter. Therefore, this thesis makes important contributions to the literature on open innovation by defining a new field for leading knowledge management experiments. It also contributes to develop a comprehensive overview of the organisational factors affecting STEs' adoption. A further major contribution is the potential value of the digital platform to innovate the services of practitioners, such as governmental agencies and consultants, that support STEs on their digital transformation journey. In conclusion, this research is valuable in opening the discussion about potential innovations that might reshape the relationship academia-business.