Research indicates that women generally populate entry-level jobs but remain largely underrepresented at the top of organizational leadership hierarchies. Within evangelical contexts, the underrepresentation of female leaders at the top is likely the result of theological bias in favor of male-centric, married leadership. The net result is that qualified single women are largely hindered from advancing to top-level evangelical leadership roles. This project aims to encourage the placement of a less-studied sector of women in leadership—single women—into top-level, evangelical leadership roles where they are rare. Based upon a review of the literature combined with data analysis, this research reveals why single women are hindered from attaining executive leadership in evangelical organizations. Female leaders experience pressures to present themselves in certain ways, are subject to others’ negative perceptions, pay painful personal costs for leading, and face persistent obstacles on their leadership pathway. Additional penalties accrue for single female leaders because their marital status contradicts both a societal and an evangelical ideal of womanhood defined by marriage and motherhood. Despite such a panoply of constraints, single female leaders display creative resilience. To encourage their number in evangelical executive roles, change must occur at theological, organizational, and individual levels. This project views single women as the most potent individual change agents and recommends a transformational, side-by-side mentoring strategy to encourage their personal development and professional advancement.