A cutting head of a waterjet cutting system is provided having an environment control device and a measurement device. The environment control device is positioned to act on a surface of a workpiece at least during a measurement operation to establish a measurement area on the surface of the workpiece substantially unobstructed by fluid. The measurement device is positioned to selectively obtain information from within the measurement area indicative of a position of the cutting head relative to the workpiece. A control system is further provided and operable to position the cutting head relative to the workpiece at a standoff distance based at least in part on the information indicative of the position of the cutting head relative to the workpiece obtained by the measurement device. A method of operating a waterjet cutting system is also provided.