Professional business-to-business sales work and relations tend to be interlinked with structures and symbols of certain forms of masculinity. From interviews held with office staff employed by a large male-dominated company in the Swedish base industry, this study explores how the gendering of sales work is enabled and contested in relation to the practices and processes of specific organizations. The presented findings show how negotiations of “good sales” involve contestations of specific gendering practices and of the value of sales work, sales relations and underlying organizational values and control. As a result, homosocial behaviors and masculine ideals associated with the salesperson no longer hold privileged positions in organizations. However, it was the individual salespersons and their behavior that were put forward as the primary problem rather than the organizational practices and processes providing men with power, space and subjectivity. Thus, the negotiations of sales work and relations seem to lead not to disruptions but to a restructuring of masculinities and to a reshaping of organizational inequalities in a company.