The increasing digitalization of business and society has prompted drastic changes within enterprises and confronted them with enormous challenges. In our exploratory interview study, we examined the impact of digital technologies on how employees work in companies as well as the specific opportunities and challenges that small and medium-sized enterprises (SMEs) face as a result. On the whole, interviews revealed that digitalization has already triggered an array of changes in how employees work. Even so, the extent of each change and the perception of technological trends overall have varied among both employees and companies depending on their context. In response to those changes, the SMEs interviewed have applied a wide range of tools and strategies that have allowed them to exploit the opportunities offered by digital technologies and overcome the associated challenges.