The capacity to deal with digital transformation is a valuable asset for established organizations, and employees play a crucial role in this process. This study contributes to the understanding of employees’ sensemaking of digital transformation in the tour operating industry. Using prior digital transformation research, construal-level theory (CLT), and dynamic change perspectives, our scholarly work focuses on the complexities of organizational change in a digital transformation context. Although employees generally support digital transformation, our findings show that their perceptions change over time across a range of specific challenges experienced during the employee change journey. Our findings stress the importance of adopting a social exchange lens in digital transformation knowledge as this represents deep structure change that might cause well-designed transformation processes to fail. Implications for hospitality and tourism management are discussed.