How does women’s political leadership training advance gender parity in public office? This project takes an ethnographic approach involving extensive participant observation and interviews to analyze and compare Republican and Democratic practitioners’ strategies and understandings of how to propel women into leadership. I use a discourse analytic framework to study candidate training programs as part of complex networks of political action and examine constructions of women’s leadership to explore broad questions about gender and power. What does it mean to lead as a woman? Interlocutors’ attitudes illuminate how entrenched sociocultural norms come to bear and at the same time become reimagined at this time of rapid social change in understandings of women’s place in U.S. politics. How do training programs and aspiring women candidates go about the transformational process of developing leadership qualities, in light of the gender ideologies and political party cultural values surrounding them? I find that partisan differences in ideological orientations to gender and leadership run contrary to what may be expected based on historical partisan commitments to the gender binary, indicating how advocates’ gender ideologies cannot be assumed based on their political ideologies. While rightwing gender-related political movements have tended to mobilize around understandings of the distinctive values of masculine and feminine in the past, leftwing groups today mobilize around gender difference and the perceived benefits of feminine leadership while simultaneously navigating the growing movement to break down sex and gender binarism. Considering political representation as a semiotic process allows for an investigation of democratic representation and electability as linked to semiotic representation, and reflective of surrounding sociocultural norms and ideologies. I intend for this dissertation to have both scholarly value and practical utility for advocates working to broaden democratic participation. I find that longer-term, cohort-based candidate training programs have the potential to build powerful social networks that serve as avenues for fundraising and mentorship and can help mitigate some external barriers to candidacy, a function that has been overlooked by other scholars.