We investigate the relationships between gender role orientations (i.e., masculine, feminine, androgynous and undifferentiated) and subjective career success among business professionals from 36 societies. Drawing on the resource management perspective, we predict that the androgynous individuals will report the highest subjective career success, followed by the masculine and feminine individuals, which in turn are followed by the undifferentiated individuals. We also postulate that the meso-organizational culture and the macro-societal business values will have moderating effects on gender role’s impact on subjective career success. The results of hierarchical linear models support the hypothesized hierarchy of the relationships between gender role orientations and subjective career success. However, we found only ethical achievement values at the societal culture level have a positive moderating impact on the relationship between the feminine orientation and subjective career success. Thus, initial findings of minimal moderation effect suggest that the meso- and macro-level environments may not play a significant role in determining an individual’s perception of career success.