PurposeThis paper explores digital transformation's impact on the work of owners in entrepreneurial firms. The interplay between working practices and technology is analyzed, taking into account the organizations' specific contexts.Design/methodology/approachA multiple case study design was applied. Eight cases of entrepreneurial firms, defined as companies that bring new products and services to the market by creating and seizing opportunities, were selected, with the goal to maximize the diversity of cases. The sample includes both small- and medium-sized firms, as well as high- tech and low- tech companies in equal number. Interviews have been used to collect both quantitative and qualitative data, which was analyzed in a structured way.FindingsThe digital transformation of entrepreneurial work, that is the daily work of entrepreneurs, is an evolutionary, practice-based phenomenon, rather than the result of rational design. The use of different digital tools is interrelated and depends on the characteristics, and dynamics of the surrounding environment.Practical implicationsThe findings of this study are relevant to entrepreneurs interested in understanding the dynamics of their working practice, to software development firms interested in entrepreneurs as customers and to institutions interested in the education of entrepreneurs.Originality/valueTo the best of the authors' knowledge this is the first study which considers the interplay between digital technology and the daily activities of entrepreneurs, considered as a whole. It provides insights on how these interconnected dimensions evolve, thus contributing to understanding the work of entrepreneurs, and as a consequence the dynamics of entrepreneurial firms in the context of digital transformation of organizations.