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If local elected offices are stepping stones to higher office, we need to better understand women’s ambition and electoral success at the local level, in order to decrease the gender gap among elected officials in the United States. We ask: are female candidates with previous experience in an elected office as electorally successful as men who have held elected office? To answer this question, we use the California Elections Data Archive, an aggregate dataset of mayoral and city council elections in California between 2008 and 2015. We find that although there is no difference in electoral success between female and male incumbents, female candidates with elected experience do worse than men with similar elected experience, when running for a higher office. Therefore, when it comes to progressive ambition at the local level, male candidates get a bigger boost from their elected experience than women. In terms of static ambition, candidate sex has no effect. But for local candidates, women's progressive ambition is stunted, relative to men's, challenging the convention that when women run, they win.