Despite extensive research on organizational virtue, our understanding about factors that promote virtue within organizations remains unclear. Drawing on upper echelon theory, we examine the relationship between five top management team (TMT) characteristics and organizational virtue orientation (OVO)—the integrated set of values and beliefs that support ethical traits and virtuous behaviors of an organization. Specifically, we utilize prospectuses of initial public offering (IPO) firms and 10-K post-IPO filings to explore how TMT composition with respect to member age, tenure, education, functional background, and gender influences OVO. Additionally, we examine the moderating effects of organizational size, and argue that the more expansive structures and processes associated with larger organizations diminish the main relationships. Our findings, using two sources of data, are consistent, but somewhat mixed in their support for our hypotheses. Overall, TMT characteristics do appear to influence OVO, but in more complex and counterintuitive ways than initially expected.