The emergence of the Chief Digital Officer (CDO) marked a significant milestone in corporate digitalization, but its role has become obsolete as digital transformation has become embedded across business functions. The CDO's limitations—vague mandates, conflicting roles, lack of measurable impact, and operational disconnect—have led to its gradual phasing out. The Chief AI Officer (CAIO) has emerged as the next leadership role, driven by urgency, technical depth, and business impact, particularly as AI reshapes the business landscape. The CAIO focuses on enterprise-wide AI strategy, requiring a stronger alignment with value creation, deeper technical grounding, and clearer execution mandates. Organizations must evolve their digital leadership logic by retiring the CDO model intentionally and embedding AI leadership in accountable roles with structural leverage. Key priorities include modernizing the digital target operating model, simplifying governance to avoid overload, and positioning AI leadership close to product and tech teams. The evolution of digital leadership will be driven from within, with clear structures and accountability being critical for successful AI implementation and future readiness.