Vicious competition and financial instability combined with rapid technological evolution and ceaselessly diversifying consumer trends are increasingly intensifying the need for contemporary organizations to continuously seek new sources of competitive advantage in their volatile operating environment. The fundamental source of sustainable competitiveness for the company of the 21st century, is its ability to constantly generate, diffuse and integrate new knowledge, and thus, to transform into learning organization. This organizational ability appears rather important in case of Knowledge Intensive Firms (KIFs), such as advertising and media companies. Due to dramatic decrease in Greek firms profitability caused by the financial recession in the last five years, these companies are required to improve their performance through more learning-and innovation-oriented initiatives. This paper explores the pattern of learning organization as well as its association with organizational performance. A questionnaire survey has been carried out, based on a sample of 330 upper level staff members who are at the helm of 163 Greek advertising and media companies. Findings have brought to light that learning-oriented operation strengthens a company's capacity for improvement through development and innovation, increases effectiveness of organizational processes, enhances relationships with customers, and finally, elevates financial performance. Conclusions have been drawn; recommendations and directions for further inquiry have been provided.