Coordinating agents to complete a set of tasks with intercoupled temporal and resource constraints is computationally challenging, yet human domain experts can solve these difficult scheduling problems using paradigms learned through years of apprenticeship. A process for manually codifying this domain knowledge within a computational framework is necessary to scale beyond the “single-expert, single-trainee” apprenticeship model. However, human domain experts often have difficulty describing their decision-making processes, causing the codification of this knowledge to become laborious. We propose a new approach for capturing domain-expert heuristics through a pairwise ranking formulation. Our approach is model-free and does not require enumerating or iterating through a large state-space. We empirically demonstrate that this approach accurately learns multifaceted heuristics on both a synthetic data set incorporating job-shop scheduling and vehicle routing problems and a real-world data set consisting of demonstrations of experts solving a weapon-to-target assignment problem.