We draw on Upper Echelons Theory (UET) to argue that CEOs face gender-specific playing fields in two key CEO role domains—corporate strategy and corporate social responsibility (CSR)—that affect CEOs’ discretion to act on their values and cognition. We attribute differences in these playing fields to incongruity between CEO role domain-based expectations and female gender-based stereotypes in the corporate strategy domain and to congruity in the CSR domain. We theorize that such situational differences pressure female CEOs to conform to industry norms in the corporate strategy domain while the CSR domain frees them to act on their values and cognition. We further test for contingencies, including gender-diverse boards and poor firm performance, that we predict will moderate the relationship between female CEOs and firm-level (non-)conformity actions in corporate versus CSR domains. We tested our predictions using a sample of S&P 1500 firms from 2007 to 2018 and found that they supported our hypotheses.