Several extant contemporary works of literature diagnose the lack of sound theoretical underpinnings of the Digital Entrepreneurship phenomenon. This paper provides a systematic literature review offering insights on the Digital Entrepreneurship phenomenon to generate insights into recent developments in the field. A systematic literature review was conducted to enhance the understanding of the phenomenon. Web of Science and Scopus were employed to identify, extract, select, and review related articles using search keywords. Finally, articles from 25 SSCI-indexed journals were selected for this study. This systematic literature review identifies current research paths on digital entrepreneurship categorizing the key findings into themes, contexts, and methodologies using the TCM framework. Finally, we propose a conceptual model that presents how a traditional enterprise can transform into a digital enterprise. The study contributes to the understanding of the conceptualization of Digital Entrepreneurship by laying the groundwork for further research development encouraging researchers to investigate this phenomenon.