This study aims to bridge the digital gender divide in information and communication technology (ICT) education and field by reflecting the alumni opinions on gender equality in the ICT context. The study aims to raise the awareness of gender equality issues through the work-life reflections. This is done to understand better the gender equality issue, and to give proposals to promoting equality also for the faculty members who teach ICT related subjects in the university. The data for the study was collected from 131 (n = 131) ICT alumni that represent 25 nationalities. Results reveal that men with 77% share dominate the closest supervisor positions and 14% of the previous ICT students in the university have felt some kind of gender-based discrimination in their work. The data-driven content analysis was used to analyze the data. In the analysis we found five main categories behind the gender-based discrimination: society, organizational; individual action; hard facts and zero. We argue, that society, organizational, and individual action proposals illustrate the digital transformation process.