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Business research on corporate leaders’ career trajectories has often focused on how female leaders differ from male leaders in terms of psychological traits and leadership styles. Yet few researchers have examined the institutional contexts and transitional processes by which women in senior management navigate their opportunities to move up or change jobs. Based on in-depth interviews with 43 women CEOs and senior managers who worked in foreign firms in Japan, this article examines how Japanese women who worked in these firms engaged in career development in order to move up to the most senior positions in their companies. The paper examines three methods by which women advanced their positions: 1) they first attained job experience in consulting firms and overseas firms; 2) they maintained relationships with and relied on their sponsors; and 3) they employed entrepreneurship skills for further career advancement or actively incorporated their entrepreneurial work in their jobs.