The issues of gender equality and gender diversity in the workplace have been intensely explored over the last few decades. There is also no paucity of studies regarding stakeholders’ influence over their organization’s contribution in these areas. The purpose of this qualitative case study was to explore in what way do stakeholders of small and midsize banks perceive the effect of an increase in the number of women in upper management or board of directors of their bank. Freeman’s 1984 Stakeholders’ Theory and Brown’s 1975 Gender Equality Theory served as the frameworks for this study. Data was collected using a qualitative case study design via an online questionnaire that was distributed by Qualtrics survey platform. The target population was owners or operators of businesses within Middlesex County, New Jersey, who utilize small and midsize banks (community banks) within Middlesex County, New Jersey, for their daily business transactions. The sample included 13 of 20 respondents who satisfied the screening criteria. Thematic analysis was employed to arrive at the conclusionary status of the investigation. For research question 1, overall, participants attributed an increase in the number of women to upper management and board of directors’ positions as a benefit to the stakeholder organization and to the women who are elevated to such positions. However, stakeholders were unable to articulate whether they perceived that such changes would affect the economic standing of their banks. A recommended course of action would be for the bank to consider stakeholders’ views and to ensure gender representation at higher levels when making staffing decisions. Recommendations for future research include in-person interviews with a sample drawn from a larger population of additional geographical locations. Also, it is recommended that future researchers should expand the demographics of the participating stakeholders to include individual customers of the bank instead of business owners/operators only. Additionally, future research should involve other genders other than the traditionally recognized genders of male and female.