Rolling shear in cross-laminated timber (CLT) has been identified as the governing factor influencing design value. Likewise, densification has been found to be an effective method of enhancing the rolling shear strength of lumber and in turn, CLT. In this study, utilizing knowledge of material properties, optimization of the compression ratio for densification has been presented. Three-layered CLT beams made from non-densified lumber, grade #1 loblolly pine (Pinus taeda L.), were subjected to a bending load at a span-to-depth ratio of eight and had a rolling shear failure at the mid-layer with a shear strength of 3 MPa. Assuming the same modulus of rupture (MOR) for both lumber and CLT made from the same species and grade, the MOR of lumber was used to calculate the minimum required shear strength (MRSS) of the transverse mid-layer to change the failure mode of the CLT beam from rolling shear to tensile failure. Using the relationship between the compression ratio and the increase in rolling shear strength, the optimized compression ratio for densification was calculated. This procedure resulted in a compression ratio of 16.67% for densification of the mid-layer to avoid rolling shear in the case of CLT beams with a span-to-depth ratio of eight. To verify this process, CLT beams with mid-layers densified at 16.67% were fabricated and submitted to a bending test. Rolling shear failure was mitigated and densified CLT beams failed in tension with a MOR similar to that of lumber, 47.45 MPa. Likewise, rolling shear strength was observed to increase by 48% for CLT that had a densified mid-layer at 16.67%.