A two-study investigation was designed to examine the role of job type (i.e. fit of political skill to work context) as a contextual moderator of the political skill–job performance relationship. Specifically, it was hypothesised that political skill operates most effectively in enterprising job contexts, and thus is most predictive of job performance in such contexts, but political skill would demonstrate no relationship with job performance in job contexts that did not emphasise interpersonal interaction and effectiveness. In Study 1, enterprising job demands interacted with political skill to affect job performance. That is, political skill positively and significantly predicted job performance in enterprising job contexts, as hypothesised. Study 2 selected one specific job context (i.e. insurance sales) high in enterprising job demands, and hypothesised that political skill would significantly predict objective measures of insurance sales (i.e. sales volume, performance-based income, performance-based commission rate, and performance-based status). The results demonstrated significant predictive effects of political skill (i.e. beyond age, sex, education level, tenure on the job, and experience in sales) on all four measures of sales performance. Contributions and implications of this research, strengths and limitations, and directions for future study are discussed.