Direct C(sp³)–H functionalization represents an attractive strategy for improving synthetic efficiency by minimizing substrate prefunctionalization and reducing synthetic operations. However, sustainable catalytic methods for the selective α-functionalization of secondary aliphatic amines remain challenging because of their high oxidation potentials and competing N-alkylation pathways. Herein, we report a visible-light-driven, switchable photoredox platform for the α-C(sp³)–H functionalization of secondary amines using a readily installed 2-iodobenzoyl (BzI) radical-translocating group. Upon photocatalytic activation, a selective 1,5-hydrogen atom transfer generates α-amino radical intermediates that can be directed toward either iminium ion formation or radical addition simply by modifying the photocatalytic cycle with an external electron donor. This catalytic strategy proceeds under mild conditions, enables direct C–H functionalization without α-prefunctionalization, and provides access to complementary reaction manifolds from a common substrate platform. Broad substrate scope, including late-stage functionalization of pharmaceuticals and biologically relevant molecules, demonstrates the synthetic versatility of the methodology. The combination of visible-light catalysis, direct C(sp³)–H activation, catalytic activation, switchable reactivity, and late-stage functionalization improves synthetic efficiency while reducing the number of synthetic operations required to access structurally diverse nitrogen-containing molecules.