The Akooda case describes the challenges confronting founder and CEO Yuval Gonczarowski (MBA '17) in 2022 as he attempts to boost sales. Launched in November 2020, Akooda was an AI company that mined 20 different sources of digital data, from tools like Slack, Google Drive, Jira, and Salesforce. Akooda's interfaces helped companies with knowledge management, process tracking, and onboarding employees by allowing managers to display real-time topics that teams and individuals engaged in during their actual work. Gonczarowski's company had begun to develop a reputation for helping companies generate insights previously obscured by the disparate software technologies used in day-to-day work. Despite strong growth, a large prospective client wanted Gonczarowski to use Akooda's artificial intelligence and machine learning capabilities to surveil, monitor, and measure the performance of individual employees. But Akooda's category was nascent, and Gonczarowski feared that providing companies with invasive monitoring tools would cause employees to distrust Akooda, hindering its ability to generate insights from employees' public-facing data. The case describes how Akooda impacts managers' roles in information-abundant but physically disconnected environments and Gonczarowski's needed to walk a tightrope between providing insights about company operations and monitoring previously private communications and activities.