Over the last several decades, cooling technologies have been developed to address the growing thermal challenges associated with high-powered electronics. However, within the next several years, the heat generated by these devices is predicted to exceed 1 kW/cm2, and traditional methods, such as air cooling, are limited in their capacities to dissipate such high heat fluxes. In contrast, two-phase cooling methods, such as microdroplet evaporation, are very promising due to the large latent heat of vaporization associated with the phase change process. Previous studies have shown that nonaxisymmetric droplets have different evaporation characteristics than spherical droplets. The solid–liquid and liquid–vapor interfacial areas, volume, contact angle, and thickness of a droplet confined atop a micropillar are the primary parameters that influence evaporative heat transport. These parameters have a strong influence on both the conduction and diffusion resistance during the evaporation process. For example, a droplet with a higher liquid–vapor interfacial area will favorably increase heat transfer. Increased droplet thickness, on the other hand, has a detrimental influence on the evaporation rate. The dimensions of these droplets will vary in response to changes in each of the aforementioned parameters. Lowering the droplet thickness can be achieved by decreasing the liquid volume while maintaining a constant solid–liquid area. However, if the solid–liquid area and volume vary simultaneously, the average droplet thickness may increase, decrease, or remain constant. Furthermore, changes in the shape of the droplet modify the local equilibrium contact angle of the droplet for different azimuthal angles. As a result, the optimal combination of these parameters must be identified to maximize the heat transfer performance of an evaporating microdroplet. These droplet parameters can be manipulated by selecting different micropillar cross sections. In this work, we develop a shape optimization tool using the particle swarm optimization algorithm to maximize evaporation from a droplet confined atop a micropillar. The tool is used to optimize the shape of a nonaxisymmetric droplet. Compared to droplets atop circular and regular equilateral triangular micropillar structures, we find that droplets confined on pseudo-triangular micropillar structures have 23.7% and 5.7% higher heat transfer coefficients, respectively. The results of this work will advance the design of microstructures that support droplets with maximum heat transfer performance.