The purpose of the paper is to examine the role of organizational conditions and managerial style in enhancing employee internal voice and brand ambassador behavior. Our approach includes a literature review of the organization and managerial context influencing employee communication behaviors with a particular focus on the retail sector. A study of a retail company based on interviews with manager, document analysis, and a survey. The main findings indicate that particular cultural conditions, such as freedom of speech and democracy, and relationships with managers, are major factors influencing internal voice behavior. Furthermore, since employees do not perform positive brand ambassador behaviors if their only commitment is continuance commitment, affective commitment is highly strategic. The study revealed that at the adoption of conceptual models that address a company's needs is an effective practice that a must be customized to the specific context and in order to sustain positive voice behavior among employee, managers should leverage an entire set of contextual conditions. This article embraces a holistic view encompassing both internal and external communication behaviors of employees, and studies their antecedents as a single set, which increases knowledge about drivers of employee communication behavior.