Are men and women equally likely to be perceived by people to possess similar requisite characteristics in comparable yet diverse occupations within management, leadership, and entrepreneurship? Because modern workplaces continue to be impacted by the persistence of varying perceptions of men and women about requisite attributes of successful people in several organizational roles, the concept of gender bias and occupational stereotypes has warranted the attention of theoreticians, scholars, and practitioners to a large extent (Koch, D’Mello, & Sackett, 2015; Kuwabara & Thébaud, 2017; Pinker, 2003; Pinker & Spelke, 2005). Although empirical evidence clearly indicates that gender inequalities in the workplace can have a significant effect on peoples’ perceptions about different characteristics of individuals in general and in specific organizational roles, there is a paucity of research examining these perceptions in a variety of leadership positions. Previous literature has investigated the gendered construction and re-construction of these professions but only to a limited extent (Gupta, Turban, Wasti, & Sikdar, 2009; Heilman, 2001, 2012; Heilman, Wallen, Fuchs, & Tamkins, 2004; Koenig, Eagly, Mitchell, & Ristikari, 2011; Kuwabara & Thébaud, 2017; Ryan, Haslam, Hersby, & Bongiorno, 2011; Schein, 1973, 1975, 2001). However, research in years past has not yet examined the full range of industry and entrepreneurial contexts that may create gender typecasting of roles. By extension, the current study focuses on how the gender-differentiated perceptions of men and women influenced the requisite characteristics of successful professional personnel in various managerial, leadership, and entrepreneurial positions. Specifically, given that these professions are influenced by gender-role expectations and stereotypes, this empirical investigation drew from role congruity theory of prejudice (Eagly & Karau, 2002) to examine the relative degree of perceived overlap between the traits associated with specific roles in management, leadership, and entrepreneurship with the traits commonly associated with men and women in general. Primary data were obtained from a diverse sample of 600 (12 x 50) working adults in the United States (N = 600, 300 women, 300 men) between the ages of 21 and 65. This was accomplished using an online survey designed via Qualtrics and administered through Amazon’s MTurk, from the lens of the classic think manager-think male (TMTM) research paradigm (Schein, 1973, 1975, 2001). The instrument used for data collection was the 92-item Schein Descriptive Index (SDI), which was used to describe sex role stereotypes and perceived requisite characteristics of twelve distinct target groups. The results of this study indicate that the perceived requisite traits of successful leaders and entrepreneurs are construed in predominantly masculine terms. These findings support and further inform the nature, existence, significance, and persistence of the “think manager-think male stereotype effect” (TMTM effect) and the “glass ceiling phenomenon” across a variety of managerial, leadership, and entrepreneurial roles, contexts, and industries. The TMTM effect was stronger among high tech entrepreneurs, CEOs, and entrepreneurs in general, whereas it was lessened for entrepreneurs in educational and health care roles, as well as for middle managers. Additionally, consistent with prior research, TMTM effects were generally either more likely to occur, or were stronger in magnitude among male raters than among female raters. These results largely support role congruity theory of gender differences in management and leadership that indicate incongruity of female gender stereotypes in general with stereotypes about high-status and prominent occupational roles in various organizations (Eagly & Karau, 2002). Specifically, the perceived trait overlap was noted to generally be stronger between men in general and successful leaders in various roles than that between women in general and successful leaders in various similar roles. The findings of the current study are expected to be valuable for those seeking to encourage opportunity regardless of candidate gender in management, entrepreneurship, and leadership, as well as for those promoting the role of women’s advancement in these professions. The study’s results have both theoretical and practical implications. Understanding these perceptions can have a significant impact on the gender biases prevalent in society, in organizations, and even across the specific entrepreneurial contexts and industries investigated within the current study. In today’s super-competitive business environment, firms must appreciate the importance of fostering equal opportunity, avoiding gender biases, and facilitating racial and ethnic diversity.