Photoredox‐catalyzed aromatization‐driven deconstructive thiolation and selenylation of spiro‐dihydroquinazolinones are presented. This method, which involves C‐C bond cleavage and C‐S or Se bond formation, provides a facile approach to synthesizing remote and site‐specific thiolated and selenated quinazolin‐4(3H)‐ones with good yields and functional group compatibility. A probable radical pathway is proposed for this transformation.