In light of the so-called globalization of business life and the expansion of transnational organizations, the concept of “transnational business masculinity” has been developed to describe a new form of masculinity among globally mobile managers. This chapter engages with this debate by focusing on gender and masculinities in the context of transnational corporate labor markets and specifically large transnational companies that are involved primarily or very substantially in knowledge work. The chapter examines the intersections of gender relations, local/national context, and transnational processes within knowledge work and management. It interrogates the complex interrelations of gender, specifically constructions of men and masculinities, with national-transnational intersections – in and between both professional knowledge work and its management and everyday lives and work-life boundaries.