Throughout the world, women are consistently underrepresented in leadership positions at the local level, even in countries with high numbers of women in national office. This report explores the context for women in local executive offices, and the unique challenges and opportunities they face in their positions. In this research, the National Democratic Institute (NDI) evaluated initial programming targeting women mayors and mayoral candidates, and conducted interviews with current and former mayors. The report details the results of that investigation, identifying trends in the experiences of women in local executive offices, and capturing lessons to inform the design and implementation of future programming. Key recommendations include ensuring a strong contextual analysis at the forefront of any program design, addressing the local candidate nomination process, strengthening women’s effective communication with the media and their communities, and building strong mentoring and support networks.