The current research examined the link between both normal and malevolent personality, proactive attitude, and self-perceived employability across some highly investigated (Belgium, Switzerland) and under-investigated populations of sub-Saharan Africa (e.g., Togo), considering proactive attitude as a potential mediator and self-perceived employability as an outcome. Conducting such a study in contexts which present notable differences in political organization and linguistic diversity, might contribute to enriching the literature on the relationships between personality and self-perceived employability. A sample of 968 participants aged 18 to 85 including 335 Belgians (50% women), 279 Swiss (58.1% women) and 354 Togolese (43.5% women) completed a French version of the Zuckerman-Kuhlman-Aluja Personality Questionnaire (ZKA-PQ/SF), Short Dark Triad (SD3), Proactive Attitude Scale (PAS), and Perceived Employability Scale (PES). All four instruments exhibited metric invariance but did not systematically show scalar invariance across the three countries. ZKA-PQ/SF's activity and neuroticism and SD3's narcissism dimensions predicted perceived employability, and these relations were fully or partially mediated by proactive attitude in all cultural contexts. Moreover, perceived employability was predicted by aggressiveness and psychopathy in the Swiss sample and by sensation seeking in both the Swiss and the Belgian samples. Finally, proactive attitude fully mediated between sensation seeking and employability in Belgium and partially between psychopathy and employability in Switzerland. This study illustrates that the link between personality and employability may be mediated by proactive attitude and that these links may be quite robust across cultures.