I looked back to other concept sketches I had from the original project and chose to go into a different direction. I wanted to imitate the shape of Colonel Sanders tie, which lead to a more elongated form. These sketches were then brought into Fusion 360 as canvas to use as a guide when creating the 3D model.
I used Fusion 360 to build an underlay model that I then took into Gravity Sketch VR. In Gravity Sketch I was able to iterate on parting lines and button layouts as if there were a physical controller in front of me. I then took orthographic screenshots and brought them back into Fusion 360 to create the final model.