School social work (SSW) is a specialized area of social work practice centered on fostering and supporting students’ academic and social-emotional readiness and success. This chapter begins with the historical origins of SSW and its implications for current practice. In doing so, the author highlights how school social workers (SSWers) bring unique knowledge and skills to the school system, strengthening the linkage between the school, home, and community, as well as directly impacting the school culture through advocacy, activism, and strategic planning. SSWers must be equipped with theoretical knowledge and anti-oppressive, culturally responsive multitiered interventions to address the various levels of need among the school community. In addition, SSWers must be committed to ongoing self-reflection and self-awareness, as one must recognize one’s positionality and be willing to dismantle assumptions, implicit biases, and blind spots to be an authentic champion of students. This chapter uses a case scenario to strengthen early career SSWers’ knowledge and application of culturally responsive, evidence-informed practices in diverse urban school communities. The chapter weaves reflective questions for advancing SSWers’ practice through the cultural competency, humility, and responsiveness continuum.