Historically, men have dominated the English football workplace; as a result, the number of women in coaching positions has been limited. The aim of the present study was to explore the lived experiences of women head coaches to identify the extent that gender influences the English football workplace. Semi-structured interviews (N = 12) were conducted with women head coaches operating at the (a) youth recreational, (b) talent development, and (c) elite levels of the English football pyramid. An inductive thematic analysis was performed which informed the development of composite vignettes, a form of creative nonfiction. Three vignettes were developed comprising women head coaches’ stories at each pyramid level. Findings from the thematic analysis identified themes of gender stereotyping, proving yourself, and confidence at the youth recreational level; work-life conflicts, limited career mobility, and marginalization at the talent development level; and tokenism, undercurrents of sexism, and apprehensions of future directives at the elite level. The vignette stories demonstrate that gender negatively influences coaches’ interactions and confidence early in their career in youth recreational football; gender bias is embedded within discriminatory organizational practices which limit career mobility for coaches working in talent development; and gender is used to hold elite level women coaches to higher scrutiny levels than male colleagues. Recommendations (e.g., [in]formal mentoring, male advocacy, recruitment transparency) are made to practitioners for a targeted occupational-focused approach regarding support, retention, and career progression of women head coaches in football.