Systems and methods for triggering generation of an alert for delivery to a remote device are disclosed herein. The system can include memory having: a user profile database; and a content library database. The system can include a recipient user device having: a network interface; and a recipient I/O subsystem; and the system can include a supervisor device having: a network interface; and a supervisor I/O subsystem. The system can include a content management server that can: direct the generation of a placement interface in the graphical user interface by the recipient I/O subsystem; direct the generation of a presentation interface; direct the generation of a coupling interface at each of the recipient user device and the supervisor user device; and generate and send an alert to the recipient user device and the supervisor device.