Over the last two decades, scholars attempted to implement models to evaluate the effectiveness of digital technologies management in healthcare organizations balanced by its compliance with sustainability. However, a managerial framework for assessing digital technologies’ contribution to healthcare organizations’ performance is still lacking. Evidence-based research on digital and mobile technologies applied in the daily life environments of people over 65 in Italy has been implemented. Results were investigated by a) SWOT analysis and b) identifying the key performance indicators to evaluate the performance of healthcare organizations by following the implementation of digital technologies in healthcare processes in a sustainable perspective. The analysis reveals that some weaknesses can be overcome (e.g., the availability of GPs to be involved in the enrollment of the patients) while others cannot (e.g., systematic limitations of digital methodologies). At the same time, some threats can be tackled (e.g., users’ and operators’ difficulty adapting to technological developments) while others can only approximately be solved. Evidenced key performance indicators can be leveraged to carry out standardized assessments related to the digital practices implemented by healthcare organizations to achieve a fully developed sustainable relational ecosystem and generate a more efficient and effective healthcare organization system.