The purpose of this study is to lay its prime focus on the support for creativity that defines the self-analysis of creative capabilities and potential among men and women. Benefitting from the cross-level interactionist perspective, social role theory, and role congruity theory, this research developed an integrated multilevel model to examine gender differences in risk-taking behavior and determine how the contextual factor of support for creativity shapes employees' risk-taking and influences their creativity performance. Data for this study were collected from 347 employees and their respective 98 supervisors of a pharmaceutical company in Jakarta, Indonesia. The proposed cross-level moderated mediation model was tested using data obtained at two points in time from two data sources (subordinates and supervisors) working at a pharmaceutical company. The obtained data were then analyzed with Mplus. Our findings indicate that women may have lower risk-taking than men in organizational contexts. However, support for creativity restores parity between men and women through cross-level moderated mediation, such that support for creativity has a stronger effect on women's risk-taking than that of men, resulting in increased creative performance for women. Research contributions and future research directions are also discussed in the relevant sections.