Online Job Advertisements (OJAs) are a valuable, detailed and up-to-date data source for analysing employers’ evolving demand for skills; therefore, they can help capture emerging trends in contexts subject to high dynamism. This paper uses OJAs to investigate the evolution of job skill requirements in Italy for occupations related to Information and Communication Technology (ICT), focusing on the educational level required in the ads. The data analysed ranges from 2019 to 2022 and covers the pre- and post-Covid period. The methodology used in the study involves a multi-step process that starts with evaluating the importance of each skill of a specific group of ICT occupations for each year/level of education combination. The skill importance indices are then used to build a measure of similarity and a measure of change in skills demand over the period 2019–2022. The primary purpose is to investigate the knowledge gap in current skills demanded by employers for each education level in a highly dynamic professional context, like ICT sector.