This STTR Phase I project addresses the challenge of upskilling the workforce by developing novel personalized content simplification technology. It will build a novel digital binder tool with an AI empowered content selection and simplification capability. The magnitude and urgency of the workforce upskilling problem require an immediate and robust solution. Corporations are desperate to find and nurture appropriately skilled workers to fill emerging roles. Beyond big high-tech corporations, the need for retraining is expanding in the trades and manufacturing space. An estimated 300-600 million people will need to be retrained between now and 2030. The proposed breakthrough solution utilizes state-of-the-art deep learning and natural language processing algorithms to automatically generate training materials appropriate for the level of familiarity that trainees have with the content and skills they need to acquire. This is facilitated by three core technologies: a content simplification solution with the capability of searching and identifying collections of digital resources by identifying key concepts. The applied algorithms consider the current background of the learner and include documents needed to comprehend those key concepts. The second technology addresses the open problem of text simplification by proposing a hybrid approach of traditional text simplification techniques like word substitution and a novel information retrieval approach that identifies concepts critical for the comprehensibility of advanced documents. The third technology is a personalized content simplification engine tailored to the needs and capacities of each trainee who can continue to use the technology for continuous retraining, upskilling and lifelong learning. This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.