Various aspects of automated grooming systems and cutting devices are disclosed. One embodiment of an automated grooming system comprises a computing device; a cutting device comprising a handle having a proximal and distal end and a cutting head positioned near the distal end of the handle; and a plurality of positioning sensors configured to send signals to the computing device relaying the position of the cutting head relative to a surface having hair extending therefrom. The computing device may be configured to receive the signals from the positioning device and prepare instructions for actuation of the cutting device. In some embodiments, the cutting device comprises a processor configured to receive the prepared instructions from the computing device and actuate the cutting device according to the prepared instructions.