Helical dichroism (HD), arising from the interaction between structured light carrying orbital angular momentum (OAM) and chiral matter, offers opportunities for enhanced chiroptical characterization at the subwavelength scale. Here, we employ inverse design to develop chiral metasurfaces tailored for enhanced HD under Laguerre-Gaussian (LG) beam illumination. The optimized planar structure exhibits a simulated HD around 115% at 800 nm for opposite OAM states, revealing the strong chiroptical response enabled by the inverse-designed geometry. The optimized metasurfaces were fabricated from Si₃N₄ and experimentally characterized using a custom-built optical system with controlled OAM excitation. A single chiral metasurface exhibited a maximum experimental HD up to 62% near 800 nm, demonstrating a strong OAM-dependent helical dichroic response from a single 6-micron-large chiral structure. Although the measured HD value is lower than the optimized simulation value, the experimental result validates the feasibility of inverse-designed chiral metasurfaces for structured-light chiroptics. These findings establish inverse design as an effective approach for engineering compact chiral nanophotonic structures with enhanced interactions with structured light, offering potential for miniaturized chiroptical sensing and OAM-resolved imaging.