The pandemic context has forced the acceleration of some major trends without developing an adequate support mechanism by the society, which determined the damage of the perception of the well-being by widely implementing teleworking. The aim of this research is to assess employee well-being correlated to professional development and competencies, autonomy, job satisfaction, commitment, emotional dimension, work-life balance and organizational climate, determined based on content analysis and customized in the context of telework. The information has been collected through a questionnaire performed in February-March 2021 and January-February 2022 in order to determine the change of perceiving in time the dimensions of evaluating the well-being and evolution trends, subject to a short period of investigation, corresponding to COVID-19 pandemic. The impact of the variables considered was quantified using the regression models. The empirical results reveal that well-being in teleworking was associated with a favorable organizational climate and with higher competencies, observing the depreciation trend of perception. We found a statistically significant positive link between job satisfaction, a favorable balance work-life and the well-being of employees. Emotional exhaustion had a negative statistically significant impact on the well-being of employees. The autonomy paradox emphasizes that a high level of it negatively affects well-being. The evolution in perceiving engagement by respondents reveals an improvement of well-being by a higher frequency of positive affects in 2022, which reconsiders the initial opinion during the analyzed period. Inclusion of the gender dimension highlights significant differences in appreciating the well-being of employees in the context of teleworking.