HRM is forced to adapt and reinvent its practices towards more innovative and creative frameworks and models, due to the impetus technological developments in the modern business environment. The same applies to the elements of the organizational culture and corporate structure, which are decisive for the success of such initiatives. To undergo the shift to digital transformation, there is a need for human resource development professionals to invest in advanced competencies and capabilities. The scope of this paper is to examine the concept of digital innovation and HRM digitalization in the shipping industry and their relationship with corporate culture, intelligence, and leadership. Data were collected via a survey conducted in Greek shipping companies, and personal interviews with maritime professionals. Findings show that organizational culture and cultural intelligence are significant factors for digital innovation. Digital culture and digital leadership are proving to be important components in achieving this, whereas organizational cultural intelligence has a major impact on e-HRM. The present research contributes at both academic and policy level. In the former case is assists in bridging the gap in the maritime literature by examining digital innovation and e-HRM practices in the shipping industry along with the required skills for their development or enhancement. In the latter case the paper assists in the documentation of challenges maritime companies face in relation to digitalization practices and how policy makers can assist in their adoption.