It is critical to pave the way for more women in science, technology, engineering, and mathematics (STEM). Despite the need for an increased workforce, women remain underrepresented in technology careers and particularly technology leadership (Tomaskovic-Devey & Han, 2018). Furthermore, there is a lack of research on how STEM recruiting and hiring practices impact female career progression and career decision making in STEM (Behroozi et al., 2019, 2020a; Friedmann & Efrat-Treister, 2023; Lunn & Ross, 2021a; S. Lunn & Ross, 2021b). The purpose of this study was to examine the career search experiences of mid-career female students and recent alumni in an online professional master's degree focused on data science who were seeking to make a mid-career change into technology and aspired toward roles in leadership. Using a qualitative approach, this study specifically considered student and recent alumni interactions with career agents (i.e., recruiters, hiring managers, interviewers) during their career searches. Four semi-structured focus groups and ten interviews were conducted with a total of 18 participants. Five themes emerged regarding the career search experiences of participants: difficulty navigating a career search labyrinth, how they valued me matters, community matters, "ambitious, but sometimes I lose hope," and aspirations as a woman in tech. This study identified how structural barriers that are unique to career search learning experiences can negatively affect female career self-efficacy while STEM self-efficacy relating to STEM learning experiences remains high. This study revealed how structural barriers can be transformed into structural supports during the career search to positively impact female career progression and career choices in STEM. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]