One of the most distinctive stylistic virtues of speechwriting is characterization, the art of capturing a client’s voice in a believable and engaging manner. This article examines characterization in the context of corporate communication, interweaving an interview with veteran executive speechwriter Alan Perlman with accounts from the ancient rhetorical tradition. As the analysis shows, Perlman’s approach to characterization confirms long-standing rhetorical wisdom yet incorporates insights that reflect the contemporary corporate context in which he has worked. The analysis also calls attention to enduring tensions in characterization—tensions between imitation and representation, effectiveness and ethics, and dramatic character and trustworthy ethos.