This paper presents a new approach combining dynamic capabilities (DCs) theory and stages of growth model theory determining that growth leaders in the insurance sector surpass pre-digital organisations operating in traditional markets due to high embedded learning capacity. I conducted nine in-depth structured interviews with senior and director-level experts working in the Dutch insurance sector. This allows for generalisability within the Financial Services sector, being very diverse: varying between pre-digital organisations and digital enterprises. This setting provides a useful context to explore how Dutch insurance businesses individually build DCs that bring about change by exploring past, current, future transformations, and reflect on what is desired from a normative perspective. Moreover, by focusing on the underlying processes and routines, I further investigated questions related to the methods, successes, risks, and failures identified at Dutch insurance companies that trigger or hinder the development of DCs for digital transformation.