IDC predicts that by 2028, 55% of enterprise training will be AI-driven and personalised, dramatically reducing time to proficiency. For CIOs in Malaysia, this signals a shift in how technology platforms must support continuous skills evolution, not just system performance. As AI-driven systems evolve faster than traditional workforce models, enterprises risk underutilising technology investments due to skills mismatch and slow capability development. This roundtable examines how CIOs and CHROs can co-create a workforce readiness layer, integrating AI platforms with skills intelligence, learning systems, and talent data to ensure employees can adapt at the speed of technology. The discussion will focus on reducing time-to-proficiency, improving system adoption, and protecting ROI from digital transformation initiatives.