Motivated by a cybersecurity application, this paper studies a two-stage, stochastic days-off scheduling problem with 1) many types of jobs that require specialized training, 2) many multi-skilled analysts, 3) the ability to shape analyst skill sets through training decisions, and 4) a large number of possible future demand scenarios. We provide a integer linear program for this problem and show it can be solved with a direct feed into Gurobi with as many as 50 employees, 6 job types, and 50 demand scenarios per day without any decomposition techniques. In addition, we develop a matheuristic–that is, an integer-programming-based local search heuristic–for instances that are too large for a straightforward feed into a commercial solver. Computational results show our matheuristic can, on average, produce solutions within 4-7% of an upper bound of the optimal objective value.