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The literature has portrayed entrepreneurial pivoting as a vital component of the lean startup approach by which entrepreneurs focus on testing and altering key aspects of their business strategy and goals. Against this backdrop, I conceptualize entrepreneurial pivoting—i.e., a change in a firm’s strategy that reorients the firm’s strategic direction through a reallocation or restructuring of activities, resources, and attention—as a potentially disruptive process that may weaken the strategic cognition of entrepreneurial team members. Drawing from representational gaps theory, I investigate the extent to which entrepreneurial pivoting undermines strategic agreement and/or understanding among entrepreneurial team members. Given that team members’ shared grasp of the pivoting allows effective implementation of the new strategy, I extend entrepreneurial team strategic agreement and understanding as predictors of team entrepreneurial performance. Furthermore, I explore factors that may accentuate or alleviate the relationship between entrepreneurial pivoting and the team strategic cognition constructs. I specifically address factors based on the following two themes. First, I focus on those that pertain to the nature of pivoting (the extent to which the pivoting decision originates more from outside of the boundary of the venture, i.e., pivot external origin, and the concreteness of the new idea toward which the venture is shifting its direction, i.e., pivot concreteness). Second, I focus on team compositional attributes (team temporal stability, team skill differentiation, and team authority differentiation). I develop and validate measures for team entrepreneurial pivoting, pivot external origin, and pivot concreteness. Then, I conduct two studies—an online panel-based study of individual entrepreneurs and a field study based on student entrepreneurial project teams at a large public university in the Southwestern United States—to test my hypotheses. My empirical findings demonstrate that the negative influence of team entrepreneurial pivoting on team strategic understanding (hence, team entrepreneurial performance) is mitigated when pivoting originates more from within the team. Also, the negative influence of team entrepreneurial pivoting on team strategic agreement (hence, team entrepreneurial performance) is mitigated when team skill differentiation is lower. Finally, I discuss theoretical and practical implications and some promising avenues for future research.