The extant literature on digital transformation, as an emerging phenomenon, has grown in volume during the last decades. As organisations continue to embrace digital transformation, in pursuit of improved efficiency of their business processes as well as the provision of better services and products to their customers, managing the necessary changes have become challenging for leaders. One of these challenges is the alignment between the IT strategy—including the introduction of new digital technologies—with the overall organisational strategy, also referred to as strategic alignment. Even though both digital transformation and strategic alignment have attracted the attention of IS researchers, there is a paucity of research exploring how strategic alignment issues play a role in the digital transformation processes undertaken by today’s organisations. To address this gap, in this study we present the findings of an empirical qualitative study conducted in two countries. Our results indicate that the action organisations take to improve their strategic alignment is dependent on how far they have come to introduce new technologies, reconfigure their business processes, and redefined their overall organisational strategy. The study provides insights on how leaders plan and implement changes in response to the changes in the external environment as well as the internal organisational dynamics.