Women now represent half the workforce but are still not progressing to leadership in equal numbers. Flexible practices can help women juggle work and non-work priorities. Although the use of flexible work practices is increasing, it is not clear if they are improving career progression. This study aimed to explore how working flexibly influences career progression. Using purposeful sampling to select male and female participants, interviews were conducted with 56 senior leaders to retrospectively explore how flexible work factors influenced their career trajectory. We found a myriad of factors that either support or impede career progression depending upon how it is used by the employee and the ways in which it is enabled by organizations. This study advances our understanding of how flexible work influences career progression and challenges the assumption that flexible work is a penalty for career success.