This article presents an autoethnographic case report based on higher education teaching activities at a Brazilian public university. It outlines significant changes in the organization of teaching work due to the technological incorporation of Web 2.0—triggered by the social isolation protocols resulting from the COVID-19 pandemic—which led to major impact on the management and outcomes of teaching activities and prompted a transition in professional identity. Compared to the pre-pandemic period, this new modus operandi relies heavily on Digital Information and Communication Technologies (DICTs). This shift has resulted in improved performance in the management and mediation of the teaching–learning process through the targeted use of these technologies in teacher training and continuing education.