During the summer of 2020, a group of Black executive directors and CEOs of Philadelphia region nonprofits began meeting informally via Zoom. In early 2021, the leadership of that affinity group (Black Nonprofit Chief Executives of Philadelphia) commissioned new research about Philadelphia-based Black-led and Black-serving nonprofit organizations. Sixteen nonprofit leaders participated in semi-structured interviews on topics including the COVID-19 pandemic, the current campaigns for racial justice and criminal justice reform, and reflection on some of the 2016 report findings. Each leader offered recommendations about how regional funders can best support Black-led and Black-serving organizations.This report documents some of the unique challenges experienced by individuals who are the first Black leaders of their respective organizations and exposes the daunting professional context endured by some Black women leaders working in the nonprofit sector.