The strategy and optimal distinctiveness literature argues that firms confront a fundamental tension between “sameness” and “differentness” in market positioning. Although an eclectic approach to this tension—that firms maintain an intermediate level of distinctiveness—has gained wide support, researchers urge further exploration of the distinctiveness-performance relationship due to contextual contingencies and the conceptual ambiguity of distinctiveness. We propose a renewed, multidimensional framework that incorporates both distinctiveness and conformity as predictors of performance. Distinctiveness measures the absolute difference between a firm and an industry’s central tendencies, while conformity captures directional differences (underconforming, mimicking, or overconforming). We outline the major assumptions in our theorizations, specify scope conditions, and empirically test our propositions in the Canadian property and casualty insurance industry. Monte Carlo simulations also validate our framework.