Rapid developments in digital innovation and technology in recent decades have marked a transition into the fourth industrial revolution (and the fifth social revolution), causing a significant impact on all areas of human activity. Moreover, these developments have been strongly felt with the advent of the COVID pandemic. The COVID pandemic has acted as a catalyst for imminent changes within the operational models of banks and their digitization, both locally and internationally, dealing with this peculiar crisis as an opportunity rather than a threat. In this study, after conducting a bibliographic overview of the key literature, an analysis of the digital development that took place in the banking sector in Greece was conducted, comparing the views of bank customers to those of bank employees and investigating the key factors that are believed to have a positive and/or negative effect on the use of new digital banking products and services, as well as the influence of factors determining digital banking expansion (gender, age, educational level, pandemic, etc.). The results revealed that bank customers were quite satisfied and familiar with digital transactions and wished to expand their use, while they considered the possibility of 24/7 service as an important factor in choosing to use digital banking, and the factors for expanding their use were transaction speed, transaction security, and information security. However, bank employees accept digital transformation positively and believe that for it to be successful, additional and ongoing training is required to upgrade their digital skills, which will also contribute to culture change and adaptation to the digital era. Furthermore, the age and educational level of bank customers had a statistically significant effect on the growing acceptance and expansion of the banking sector’s digital transformation. A comparison of the correlations of the demographic data with answers given by bank employees did not reveal any significant variations regarding the findings given by bank customers. These findings can be useful for bank management policy-making issues, for banks and their supervising authorities to build KPIs to monitor and assess the digitalization progress, and for academics for further research, especially as the COVID pandemic ensues and the need for digital solutions is all the more urgent, marking the digital competition between banks as one of increasing intensity.