Concerns about corporate scandals and abusive leadership suggest that individuals with an opportunistic and manipulative personality sort into managerial positions. Indeed, a fledgling number of econometric studies have shown that individuals high in Machiavellianism are more likely to hold a management position. Our study takes that research an important step further by analyzing the moderating role of gender. It examines whether gender has an influence on how far Machiavellians climb the managerial hierarchy. Using representative data from Germany, we find that Machiavellianism increases the likelihood of holding a middle management position for both men and women. However, Machiavellianism is associated with a higher likelihood of occupying a top-level management position only among men but not among women. For men, the impact of Machiavellianism even appears to increase the further they climb the managerial hierarchy. These findings fit theoretical considerations.