Digital transformation, or digitalization, is a near-ubiquitous concept in the contemporary insurance business ecosystem, and describes the work towards change that is carried out in insurance organizations towards novel, digitally empowered practices, services, and management structures. Large-scale studies have identified key factors for successful digital transformation as, among others, customer experience, digital development, and changing business processes. This case study investigates a customer-owned Finnish insurance company that currently resides in the nascent stages of such a transformation. Through a set of 13 interviews with 10 service developers and managers, we set out to understand and evaluate their current digital development practices, based from the perspectives of participatory design, towards informing marketing research. Our findings indicate that while there exists a general understanding of the value of user involvement in the design process, participatory design practices see limited implementation, and there is an apparent disparity between the customer-centric organizational culture and the development practices that it should inform. We suggest work to be put towards the creation of models for evaluating digital transformation, and towards aligning the management of the digital transformation process with a participatory mindset.