In various embodiments, a dynamically directed workpiece positioning system may include a transport, a sensor positioned to detect a workpiece on the transport, a cutting member positioned along or downstream of the transport, and a computer system. The sensor may scan the workpiece as the workpiece is moved relative to the transport by a human operator or a positioning device. Based on the scan data, the computer system may generate commands to guide the human operator or positioning device in moving the workpiece to a desired position corresponding to a cut solution for the workpiece. Optionally, the computer system may cause the cutting member to be repositioned while the workpiece is being moved relative to the transport. Once the workpiece is in the desired position, the transport may be used to move the workpiece toward the cutting member. Corresponding methods and apparatuses are also disclosed.