During the past two years, the US Air Force (USAF) Air Education Training Command (AETC) graduated 26 pilot candidates from an experimental Undergraduate Pilot Training (UPT) program called Pilot Training Next (PTN). AETC envisioned PTN as an aviation-centric use case for a greater “Learning Next” initiative, oriented on changing how institutions instill requisite knowledge and skills effectively using the latest commodity technologies. Working in collaboration with the Aviation and Missile Center under the US Army Combat Capability Development Command (CCDC), Army Futures Command, AETC trained two separate cohorts of PTN students using similar paradigm-changing methodologies but with different execution. The focus during the first cohort was to make training tools more accessible using creatively-applied commodity Commercial Off the Shelf (COTS) systems and sensors. The focus during the second cohort was to holistically revamp the learning environment to enable self-improving competency-based learning rooted in solid data analytics. Competency-based learning is a game-changing shift for AETC that will help create aviators who are skilled pilots as well as self-directed learners and critical thinkers who can adapt to complex and changing adversarial tactics. This paper discusses the execution of the second PTN course with a focus on how AETC and CCDC created PTN’s learning framework and how it can evolve based on data collected from the learning environment. This paper provides specific examples of how collected data transform into insights for the curriculum, using both traditional analytics workflows and industry-standard learning technology specifications. It also describes the technical solutions in place for the Learning Management System (LMS), Learning Record Store (LRS) and automated visualization workflows as well as the types of simulated flight, biometric and proficiency data the program collected. Finally, this paper discusses lessons learned regarding data collection, correlation and availability that are critical to the success of any data-backed curriculum development.