In the last years, smart working has been introduced as an agile and dynamic way of working which provides high levels of performance, productivity, and job satisfaction in a “triple-win” configuration for customers, employees, and organizations. Although the advantages and disadvantages related to these new working practices have been recognized by the literature, how these new work practices, widely adopted during the Covid-19 pandemic, have been generally perceived on a massive scale is still unclear. Based on these considerations, this work aims to carry out a big data analysis in order to frame the collective perception about smart working. A large-scale text analytics study has been conducted on Twitter from January to June 2021. The data-driven approach identified the most frequently used macro-concepts about smart working by Twitter’s users: five perceived in a positive way (smartness, work-life balance, flexible approach, productivity, innovative working environment) and five perceived negatively (tech paralysis, technostress, technology hiccups, demotivation, social isolation). In this sense, the study offers several insights by generating useful implications for researchers and professionals both in the organizational design and psychological and Human Resources Management field.