Insertion devices and associated systems and methods for the percutaneous placement of patient leads are disclosed herein. A system in accordance with a particular embodiment includes a cannula having a lumen and a first dilator. The first dilator can be positioned within the lumen and the first dilator and the cannula can be used to create a percutaneous entry point. An additional dilator can be positioned over the first dilator and advanced into the percutaneous entry point to expand the percutaneous entry point. A final dilator can be inserted into the patient and two leads can be advanced into the patient through the final dilator.