This paper brings to cognizance the challenges faced by women in the male-dominated occupation of sales. A qualitative phenomenological approach was used to decipher lived experiences of 10 female participants working with sales teams in different industries. Semi-structured in-depth interviews were analysed using Interpretative Phenomenological Analysis. The research was conducted with the lens of social-role theory braced with sales taxonomy and occupational segregation literature. The study reveals gender identities that prevent women from crossing over to masculinity, quandary of heterosexual relationships and sexual advances from within the organization and market. Finally, women share their coping mechanisms and mitigation methods for overcoming the perplexities and sustaining in the occupation.