Faced with the combined force of the COVID-19 pandemic and digital transformation, a plethora of organizations have allowed their employees to work from anywhere, as a ubiquitous organizational phenomenon, thanks to which the workforce can work, connect, communicate, and collaborate virtually. Employers and employees debate: the former prefer office presence, while the latter may favour remote work flexibility. Productivity is often at the heart of this debate. Based on a search in the Scopus database, no similar research was found that explores the factors affecting productivity in the digital workplace, representing an additional motivation for the authors to carry out the research. Therefore, this book chapter aims to identify the human and organizational factors affecting productivity in the digital workplace and investigate their positive or negative influence on employees’ productivity. The book chapter presents a research model grounded in a literature review and a theoretical triangulation of the person–environment fit, social information processing, and open resource-based view theories. From the methodological aspect, a machine learning model for multilinear regression analysis is used based on survey data. The book chapter highlights the enabling factors of productivity in the digital workplace, holding potential implications for researchers, practitioners, and policymakers, who express substantial interest in how productivity in the digital workplace can be enhanced.