This contribution applies the worldwide-ongoing phenomenon of digital transformation to a specific industry and HR function. However, many companies and their employees are struggling to adapt to this significant change. Focusing on one particular area within the HR department, Learning and Development (L&D) in an international organisation, this study concentrates on the assessment and transformation of manual processes into digitalised methods. The emphasis is on digital synchronisation of L&D. The main aim is to comprehend the bottlenecks of digital transformation and propose possible solutions to mitigate the challenges. The objectives of this study are therefore proven by the empirical data collected from interviews and qualitative case studies. This study will provide guidelines to organisations to kick-off digital transformation process aiming to integrate into a global community.