This study investigated the optimal shape of glue-laminated timber beams using an analytical model of a slender beam, taking into account the anisotropy of its strength properties as well as boundary conditions at the oblique bottom face of the beam. A control theory problem was formulated in order to optimize the shape of the modeled beam. Two optimization tasks were considered: minimizing material usage (Vmin) for a fixed load-carrying capacity (LCC) of the beam and maximizing load-bearing capacity (Qmax) for a given volume of the beam. The optimal solution was found using Pontryagin’s maximum principle (PMP). Optimal shapes were determined using Dircol v. 2.1 software and then adjusted according to a 3D finite element analysis (FEA) performed in Abaqus. The final shapes obtained through this procedure were used in the CNC-based production of three types of nine beams: three reference rectangular beams, three Vmin beams, and three Qmax beams. All specimens were subjected to a four-point bending test. The experimental results were contrasted with theoretical assumptions. Optimization reduced material usage by ca. 12.9% while preserving approximately the same LCC. The maximization of LCC was found to be rather unsuccessful due to the significant dependence of the beams’ response on the highly variable mechanical properties of GLT.