As the aerospace and defense industry strives to embrace digital engineering transformation, organizations quickly realize that this transformation is much more than just tools or infrastructure. It requires comprehensive change that involves people, process, and technology, and that calls for organizational strategy and stakeholder commitment. This paper provides an overview of an on‐going corporate initiative to develop an enterprise‐wide, model‐based systems engineering (MBSE) and model‐based engineering (MBE) capabilities and to instantiate a transformation of legacy workforce and culture. Our vision is to apply digital engineering (DE) as an enabler to transform legacy, document‐based development stovepipes into a product‐centric, integrated, digital engineering enterprise. At the implementation level, however, it involves a multipronged investment strategy in technology, infrastructure, process, and people, as well as an incremental process of learning and experiments. This paper lays out the architectural vision, implementation approach, and the business rationales. It also attempts to reflect on the journey to date, discussing some of the early successes, hurdles and challenges in implementing the digital engineering initiative for a diverse defense services business.