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This paper examines the lives and leadership practices of three Black women “firsts”-- Yvonne Conolly (London, 1969), Betty Campbell (Cardiff, 1973), and Gertrude Paul (Leeds, 1976) —who were pioneer women head teachers (school leaders) in the UK in the 1960s and 1970s. Black Feminist Thought (Collins, 2000), Black British Feminism (Mirza, 1997: Ali, Mirza, Phoenix, & Ringrose, 2010) and intersectionality (Agosto & Roland, 2018; Brah & Phoenix, 2004) are utilized as theoretical frameworks to interrogate how these Black female school leaders crafted a self defined leadership stance as “outsiders within” and navigated the educational establishment to successfully advocate for the opportunities and life chances of African Caribbean and immigrant students and their families in an often hostile British educational environment.