An embodiment includes parsing form data into a plurality of form values received with a schedule request and assembling the form values into a search vector. The embodiment searches historical data using a nearest neighbor algorithm that inputs the search vector and identifies first and second sets of historical vectors comprising that are closest by Euclidean distance to the search vector. The embodiment calculates an enhanced constraint vector comprising an average value based at least in part on the first set of historical vectors and a standard deviation value based at least in part on the second set of historical vectors. The embodiment generates an employee schedule using an optimization algorithm subject to a plurality of schedule constraints that include the enhanced constraint vector. The embodiment then transmit data for initiating a notification regarding availability of the employee schedule.