The aim of this study is to gain insight into the gender‐specific career advancement of about 10,000 middle‐ and top‐level managers in a Dutch financial services company. Our results indicate that women earn less, work at lower job levels, but show slightly higher career mobility than men. However, working a compressed four‐day nine‐hours‐a‐day workweek turns out to be favourable for women who are ‘rewarded’ for working full time, whereas men are ‘penalized’ for not working five days a week. Introducing this form of flexibility into a predominantly masculine organizational culture offers new opportunities for career advancement, albeit solely for women.