Systems and methods are provided for allocating resources in harvest operations involving multiple fields and multiple pickers. One example computer-implemented method includes retrieving data specific to a harvest project and, for each of multiple stages for a site of the harvest project, determining, via a decision service, multiple potential allocations of the multiple pickers to fields of the site based on the retrieved data and one or more applicable constraints, advancing one or more of the potential allocations based on a determined parameter, and imposing at least one constraint consistent with ones of the one or more advanced potential allocations. The method then includes determining, via the decision service, at least one allocation of the multiple pickers to the multiple fields based on the retrieved data and one or more applicable constraints, compiling and storing a harvest plan for the harvest project, and implementing the harvest plan.