The article focuses on women who are members of the Boards of Directors in Italian listed companies, namely they hold a top position for which women representation has been guaranteed by gender quotas since 2011. Through a web survey, we investigated their perceptions on the main obstacles to the top-level female careers and the effectiveness of gender quotas in tackling gender inequalities. Our findings suggest that: i) career discrimination suffered by women is multidimensional, with factors attributable to the demand side playing a major role (i.e. homosocial reproduction of power); ii) gender quotas appear to be necessary to ensure an adequate women's representation at the highest management level, but not sufficient to trigger a corporate change in gender equality policies affecting all workers; iii) perceptions on these topics are influenced by personal career paths: women who have not benefited from gender quotas tend to underestimate gender discrimination, while women who have reached top positions thanks to quotas emphasize the structural nature of gender inequalities.