This phenomenological research study explores how districts in Massachusetts support and hinder the work of professionals in the inaugural role of Director of Diversity, Equity and Inclusion (DE&I). Through a qualitative approach, the study engaged six Directors of Diversity, Equity and Inclusion from suburban and urban school settings in semi-structured interviews and focus groups. The data analysis revealed several key themes including the challenges of managing ambiguity and uncertainty of the role, the urgency for supporting BIPOC stakeholders, the emotional toll that comes from a focus on racial issues, and the difficulties of navigating resistance from within and outside of the school district. Overall, the findings suggest that districts should consider creating and utilizing standards for practice to clarify the work and function of Directors of Diversity, Equity, and Inclusion. Further, investing in developing coaching skills in these directors will allow for transformational work to take place within the organization. Instituting self-care supports similar to clinical supervision models may combat the racialized stress experienced by these practitioners. Lastly, the researcher recommends that senior district leaders such as the superintendent become the lead voice organizing and communicating equity goals and initiatives within the district.