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A visible‐light‐enabled catalytic intermolecular azido‐hydrazination method for unactivated alkenes is developed via an orderly radical addition sequence. This transformation features metal‐free and redox‐neutral conditions and is applicable to a wide range of alkenes with commercially available reagents. Mechanistic and kinetic studies reveal that the efficient generation of azide radical enabled by fluorenone under visible‐light is critical to this methodology. The β‐azido alkyl hydrazines prepared with this reaction can be conveniently derived to valuable synthetic building blocks, and one of the products has been successfully applied in the total synthesis of (±)‐ibrutinib, which is used to treat B cell cancers. [ABSTRACT FROM AUTHOR]