Techniques and technologies for caller assistance systems are described. In at least some embodiments, a system comprises: a processing component; and a caller assistance engine configured to receive a request from a calling device; select a menu execution path associated with the request, the menu execution path defining one or more operations to be performed to achieve an intent of the request; execute the menu execution path including execute the one or more operations to be performed to achieve the intent of the request; determine whether the intent of the request has been achieved; and when the intent of the request has been achieved, connect the calling device with the intent of the request or provide an alert to the calling device that the intent of the request has been achieved.