How do firms differentiate themselves from others, and how do audiences respond to their distinctiveness? Optimal distinctiveness theory suggests that an intermediate level of distinctiveness in a single point or a balance in the level of distinctiveness across multiple points is most beneficial to a firm as it addresses both competition and conformity pressures. However, empirical studies have found positive, inverted U-shaped, and U-shaped relationships between distinctiveness and audience evaluation. Using CSR strategy as a research context, I develop a theory of two forms of distinctiveness—positioning distinctiveness and topic distinctiveness—and explore each form’s unique and interactive effect on audience evaluation. Building on cognitive categorization research, I argue that positioning distinctiveness, or the extent to which the pattern of resource allocation across an established set of strategic decisions differs from that of category prototypes, will have a positive relationship with subsequent audience evaluation. However, topic distinctiveness, or the extent to which a firm differentiates itself from others by introducing new practices to its category, will show an inverted U-shaped relationship with audience evaluation. I also examine how positioning distinctiveness moderates the effect of topic distinctiveness and predict that audiences will assess a firm’s topic distinctiveness more positively when a firm has a high level of positioning distinctiveness in its main topic domain. In addition, I investigate how strategic distinctiveness in business strategy and environmental-level factors moderate the effects of positioning and topic distinctiveness by influencing audiences’ demands for differentiation and conformity. Utilizing the sample of S&P 500 firms from 2001 to 2018, I empirically examine the hypothesized relationships. By analyzing annual CSR reports using state-of-the-art natural language programming and topic modeling techniques, I develop a novel measure of topic distinctiveness in CSR strategy. This dissertation contributes to the optimal distinctiveness literature by simultaneously examining multiple forms of distinctiveness and by unpacking the conditions under which demands for conformity and differentiation may vary.