In 2019, Oakland teachers joined the wave of teacher strikes across U.S. cities sparked by teacher activism against neoliberal reforms that cut funding to public schools, increased privatization, and led to school closures. As in other cities, a group of progressive rank-and-file teachers working toward transformative change moved their union toward social movement unionism, and in the process, garnered the support of communities of color that had been alienated from organized teachers. Drawing on in-depth interviews with teacher activists involved in the 2019 Oakland teacher strike, I demonstrate how strategic decisions to focus on gaining power within the union and to center the leadership of progressive teachers of color, especially women of color, helped to build public support for both the strike and the broader movement against privatization, yet also led them to focus on an inside strategy that may undermine their more transformative goals. I argue that as activist teachers gain power within their unions, activist groups that function independently from the union provide a critical outside space where teachers can develop an intersectional and transformative praxis that helps them better strategize against the racial politics of advocacy in the neoliberal context.