Although literature shows that gender discrimination in science and technology persists in many countries, there is still a lack of research on factors influencing the external engagement of female academics. This chapter provides a cross-country comparison regarding the influence of gender on academic roles and engagement in third mission activities. Focusing on four countries from the Baltic Sea region of the European Union—Estonia, Finland, Lithuania, and Sweden—we examine the impact of institutional factors, including contractual arrangements, institutional expectations, as well as considerations for career advancement, on the external engagement of male and female academics in the soft sciences. Our findings show that traditional gender patterns are challenged within the soft sciences in selected countries of the Baltic Sea region, with female academics being more likely to engage in external activities than males. While institutional expectations to take research beyond traditional publication are strongly pronounced in some of the case study countries, they are only marginally and negatively related to external engagement. The perceived importance of external engagement to career advancement is, however, positively related to time spent on external engagement, especially during teaching-free periods.