Why can some organizations acquire more new customers or more successfully retain existing customers than others? Although various organizational constructs illustrate situational contingencies to strategic behaviors, we argue that entrepreneurial orientation (EO) and customer orientation (CO) still warrant considerable theoretical and practical attention in the domain of corporate entrepreneurship. To address this, our study first identified a research model that can delineate the sequential impact of meaningful work encompassing EO (CO) on customer-oriented outcomes. Our conditional indirect framework attempts to specify both how and when the effects of EO (CO) occur when acquiring new customers (retaining existing customers), so that our study contributes to the development of task characteristics theory and the actual application of the input-mediator-output (IMO) framework via the dispersion of EO (CO) in organizations.