The banking sector has been a leader in digital transformation processes. Internet banking services, cloud computing, chatbots, and artificial intelligence services are some of the technologies used to provide better customer service and experience, cost reduction, and consequently, growth and profitability to banks. Due to the acceleration of digital transformation, there is a growing need to assess banks’ digital maturity levels in various national frameworks. The proposed research examines the digital maturity level of Greek banks and the degree of employee adaptation to digital transformation. This study is a pilot study and part of a broader research. Data were collected by applying a structured questionnaire on a convenient sample of 60 employees coming from all four Greek systematic banks, from March to June 2024. Results are based on the ANOVA analysis, which determines employees’ adaptation to digital transformation based on several characteristics. Results indicate higher degrees of adaptation between senior executives, while middle and lower levels of executives seem less ready to adapt. Moreover, executives coming from non-banking sectors are ready to adapt, while longstanding bank employees seem less flexible. Finally, the degree/level of digital maturity in the banking sector can predict the degree of employee adaptation. The study aims to help the banking sectors provide useful information to senior management and decision-makers regarding digital transformation and their employee’s adaptation, revealing that it is mainly a top–down process that relies primarily on corporate executives, who, however, come from diverse professional backgrounds.