Drawing on generational theory, we argue that family millennials' involvement is a driver of export intensity in family firms, but it depends on two different CEO characteristics, namely: family membership and societal generational membership. An ordered probit regression analysis on 92 Italian family firms confirms that the involvement of family millennials positively influences export intensity and that a millennial CEO enhances that positive effect. In addition, we found that a non-family CEO amplifies such a positive effect, whereas a family CEO tends to turn the tide so that the effect of family millennials' involvement becomes negative. The novel findings of our explorative study contribute not only to the research on family business and internationalization, but also to the literature on generational theory.