This article features interview excerpts from 10 Black women who worked as educators in marketized cities and schools, including urban charter schools operated by charter management organizations, and independent schools, known as standalone charter schools. Using a critical race policy framework, the article considers the pedagogical implications of race, gender, and power embedded in market policies and which shaped the women's experiences in their schools. Key dilemmas for the women included: limited resources in district schools, lack of autonomy in privately managed charter schools, and difficulties enacting critical and culturally inclusive pedagogy in market settings premised on individual competition and test score production. As several of the women left their charter schools, or the profession altogether, their experiences map onto larger concerns with Black teacher turnover and decline in urban districts embracing marketization of public schools. The article ends with three broad strategies to support Black women in market settings.