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Today, newly founded businesses are inevitably driven to start in a digital form from day 1. Moreover, most existing businesses conceive digitalization as an important part of their strategic orientation by developing and improving their digital assets and digitalizing their processes. By taking account of this development, this chapter investigates how entrepreneurial orientation (EO) affects a small firm’s proclivity to both digitization and internationalization and their performance that comes from it. Internationalization has been a key topic for many small- and medium-sized companies (SMEs) over the past decades. As digitization is currently taking over the helm from internationalization as the most pressing topic affecting business, we carried out research among SMEs to understand the interplay of these factors influencing business performance. The focus of the research was on the precursory factors inducing firm performance as well as on their interrelationships. Using a sample of 357 SMEs, EO is found to be significantly closely associated with an SME’s degree of digitization as well as with its overall performance. In contrast, EO does not affect the SME’s level of internationalization. This result is surprising considering that proactive and risk-taking firms tend to be more inclined to enter foreign and distant markets.

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