Nowadays, all organizations face increased global competition in a knowledge-based economy. Consequently, they need to continually learn and convert their project-derived knowledge into enhanced and innovative products and services in order to remain competitive in an increasingly aggressive market. Knowledge is not merely widely regarded as a key asset in companies, but it is becoming the most critical strategic determinant of economic growth. This study investigates possible correlations between the adoption of knowledge management systems, complexity of the working environment and digitalization. It investigates any correlation between complex working environments and systems of knowledge management, between specific organizational context and level of digitalization. The study has been developed with the start of a structured online survey sent via e-mail to a selected target working in companies located in Switzerland and Northern Italy and operating in different sectors, whose size range from small, to mid-size to large, including both local and global organizations. It consisted of 19 closed questions grouped in 4 main KPI (Complexity, Digitalisation, KMS, Organisational Context) aimed to gain a relevant insight on knowledge management practices and digital transformation topics. The overall picture that emerged shows that organizations with high KPI for digitalization, knowledge management systems and organizational context are tendentially young, small, from tertiary sector and with national customer base. Moreover, the survey demonstrates a strong interconnection between the 3 KPIs organisational context, digitalisation and adoption of knowledge management systems. Organizations should therefore encourage the creation of knowledge and endeavour to invest in tools and technologies necessary to support processes involved in knowledge management