The necessity of learning is essential for every organization to realize the full potential of the workforce. But many organizations treat learning like training or academic instruction to ensure policy or compliance to a minimum level of work performance, instead of continuing career education and improving skills in the operational workflow. The context for where and how workers work is critical to ensure that on-the-job learning is possible. While traditional learning management systems (LMS) have advanced the authoring and curriculum for formalized training in a digital learning environment, the need to adapt learning to the operational requirements is essential for every organization. This context provides the opportunity for continuous skills development, which is essential to building organizational readiness and workforce resilience critical for everyday operations and business continuity. We assert that by 2024, learning management systems and learning experience platforms with embedded skill and job ontologies that recommend optimal learning paths will guide one-half of organizations to elevate employee engagement, retention and productivity.