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This study examines the Women of Color Education Collaborative (WOCEC), a professional association for women of color district leaders aspiring to or currently holding the superintendency as a distinctive context for advancing district leadership diversity. We investigate how members perceive WOCEC's programmatic features as counterspace challenge processes (Case and Hunter, 2012) and mechanisms for enacting their community cultural wealth (Yosso, 2005). We find three prominent counterspace processes (narrative identity work, direct relational transactions, and acts of resistance) and four types of cultural capital associated with community cultural wealth (aspirational, navigational, social, and resistance) within the association. These findings have implications for enhancing the retention of women of color superintendents and advancing asset-oriented cultural capital theory.