With significant shortages of employees and managers are cybersecurity and technology management, the need for more professionals in the field has never been more critical and necessary. Meeting these workforce development shortfalls and developing innovative business strategies requires leaders from all genders and backgrounds. To effectively achieve the most challenging concerns related to organizational technology management strategy will require the contributions of women. This paper explores the barriers, complexities, and innovative approaches related to developing more women in executive and supervisory roles in information technology and cybersecurity.