As digital technologies increasingly enter organizations through various points of entry—rather than solely through gatekeepers—it is essential to examine how these technologies are explored by various individuals and groups before formal organizational adoption. Through a qualitative field study of 24 organizations piloting a digital labor platform, we find that the locus of entry—whether gatekeepers or non-gatekeepers initiate exploratory use—shapes how technology components are curated, resisted, or embraced. Gatekeepers prioritize features that enhance their control, while excluding those perceived as a threat, leading to selective adoption or abandonment when the technology fails to integrate well with existing workflows. Conversely, non-gatekeepers explore platforms outside centralized processes, bypassing gatekeeping constraints. Their success in adopting the technology depends on either engaging gatekeepers proactively or strategically concealing their use to avoid resistance. These findings reveal that technology adoption trajectories are not set by single decisions, but through an evolving process, where both gatekeepers and non-gatekeepers actively shape these trajectories through curation, resistance, and power negotiations, ultimately shaping the trajectories through which the technology is integrated into organizational processes.