Amidst the prevailing scarcity of personnel and leaders within healthcare cybersecurity and technology management, the demand for bolstering the ranks of professionals in these domains has reached unprecedented significance and urgency. Enlisting women leaders and those from diverse backgrounds is imperative to address the deficiencies in workforce development and devise pioneering business strategies. The endeavor to effectively confront the most formidable issues about organizational technology management strategies necessitates women's active participation and contributions. This chapter embarks on a comprehensive exploration of the hurdles, intricacies, and innovative methodologies pertinent to the advancement of women into executive and supervisory positions within the domains of information technology and healthcare cybersecurity.