With the goal of improving assessment of interests toward social and enterprising areas, we developed the Vertical Social Interest Scale (VSIS) by incorporating vertical differentiation between occupations in terms of authority and communication. Social and enterprising occupations, their complexity levels, and work activities were identified using the information in the Dictionary of Occupational Titles and Occupational Information Network. Three studies (N = 515 total), two of which utilized students and one a working adult sample, were conducted to assess the factor structure and validity of VSIS. Construct validity was demonstrated using factor analyses and based on associations with traditional interest assessments and extraversion. Criterion-related validity was demonstrated based on associations with satisfaction with academic domain for the student sample and affective occupational commitment for the adult sample. Results support the validity of VSIS in predicting relevant vocational outcomes.