Based on interviews with twenty women hospitality leaders, this report explores what hospitality firms can do to facilitate the advancement of women into the ranks of top leadership. Drawing on the respondents’ observations in semi-structured interviews, we argue that organizations would likely strengthen the retention of their professionals, especially female professionals, if top leaders make a deep commitment to reevaluate and potentially revise current processes and structures. This commitment includes refocusing on purposeful long-term career development that provides a sightline to the top, and ultimately creates more female role models in executive-level positions. Organizations would also benefit from offering autonomy over how work is completed, and designing infrastructures of support to assist professionals during mid-career stages. Hospitality firms that take tangible, consistent, and systemic action that is executed by motivated and supportive leaders will stand the best chance of retaining a valuable resource—their female professional talent—and benefiting from that expertise.