We report a general visible-light-mediated strategy that enables the construction of complex C(sp(3))-rich N-heterospirocycles from feedstock aliphatic ketones and aldehydes with a broad selection of alkene-containing secondary amines. Key to the success of this approach was the utilization of a highly reducing Ir-photocatalyst and orchestration of the intrinsic reactivities of 1,4-cyclo-hexadiene and Hantzsch ester. This methodology provides streamlined access to complex C(sp(3))-rich N-heterospirocycles displaying structural and functional features relevant to fragment-based lead identification programs.