Australia and Canada have recently witnessed a rise in the number of women Premiers, the top political job at the sub-national level. Prior to 2007 only two women served in the premier’s post in each country’s entire history. But since 2007, eleven women have moved into the Premier’s office, making a total of eight in Canada and seven in Australia. Six of Canada’s ten provinces and five of Australia’s six states have seen a woman in the premier’s office. Moreover, six premiers have kept their parties in office by winning elections and three have led opposition parties to victory. These achievements stand in contrast to the global trend of women’s significant and continued under-representation in national political leadership roles (Skard, 2014). Research on women’s political advancement consequently focuses on answering the “why so few?” question. By contrast, the relative abundance of comparable subnational government leaders in Canada and Australia allows us to switch the focus from women’s absence to women’s presence and investigate the conditions facilitating success for women. Political careers are necessarily shaped by the interplay of individual factors and institutional design, but in this paper we argue that the representative context also matters. In both parliamentary and presidential systems a hierarchy of political offices serves as a career ladder for candidates and elected officials, such that when women enter lower levels of political office in greater numbers, they are more likely to be promoted to higher levels. Political experience and credibility also positions women within networks that inform cabinet selection and party leadership contests. Our paper measures women’s levels of representation as legislators, cabinet ministers, political party leaders and premiers in each of the ten Canadian provinces and six Australian states from 1980 to 2017. Mapping the numbers of women elected, establishing where they are located in the legislative hierarchy, and making comparisons over time and by jurisdiction allows us to examine the utility of the “pipeline” theory and the political-cultural milieu in explaining how women’s political careers take shape at the sub-national level.