Metallo-photoredox catalysis has redefined the available bond disconnections in the synthetic arsenal. By harnessing the one-electron chemistry of photoredox catalysis in tandem with low-valent cobalt catalysts, new methods by which functionalities may be stitched together become available. Herein we describe the coupling of photoredox-generated alpha-amino radical species with conjugated dienes using a unified cobalt and iridium catalytic system in order to access a variety of useful homoallylic amines from simple commercially available starting materials. We present a series of mechanistic experiments that support the intervention of Co-hydride intermediates that undergo diene insertion to generate Co-pi-allyl species.