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While Saudi Arabia’s ongoing economic diversification strategies are breaking down the institutional barriers to women’s entrepreneurship, they are also changing the gender segregation that previously enabled some successful outcomes for women entrepreneurs. To understand how women entrepreneurs can thrive in the forward-looking, “new,” gender inclusive Saudi Arabia, we need to reflect upon the “old,” gender-segregated Saudi Arabia. We carried out a qualitative study with thirty women entrepreneurs to explore this transition from old to new. We pinpoint five managerial and entrepreneurial implications of the gender reforms that are taking root. Furthermore, this country-specific focus on a unique entrepreneurial place challenges the mainstream US-Eurocentric approach to the treatment of gender issues in terms of segregation and inclusivity.