Career stories of 50 female executives from major corporations and high-growth entrepreneurial ventures suggest two alternative accounts of how women legitimize their claims to top leadership positions: navigating and pioneering. In navigating accounts, the women legitimized their claims to top authority positions by following well institutionalized paths of career advancement (e.g., high performance in line jobs) and self-advocating with the gatekeepers of the social hierarchy (e.g., bosses, investors). In pioneering accounts, the women articulated a strategic vision and cultivated a community of support and followership around their strategic ideas and leadership. The career stories suggested that, when the women’s authority claims were not validated, they engaged in narrative identity work to revise their aspirations and legitimization strategies. Sometimes narrative identity work motivated women to shift from one type of account to another, particularly from navigating to pioneering. Based on inductive analyses of these 50 career stories, I propose a process model of how women legitimize their claims to top leadership positions by recursively resetting career accounts as authority claims succeed or fail.