The uptake of digital solutions can significantly foster the transition towards circular and sustainable value chains and territories. Such solutions can help to effectively assess the circularity performance while ensuring the lowest environmental, economic, and social impacts. Thus, it provides decision-makers of considered organisations, i.e., both industries and territories, with a holistic vision of the actions they are willing to adopt. The newly proposed Circular Digital Cockpit (CDC) intends to enable the development of these types of digital solutions. Indeed, this conceptual framework aims to provide a systematic approach for measuring circularity, facilitating well-informed decision-making, and targeted interventions. The present paper proposes a comparative analysis of five industrial and territorial organisations to underline variants and invariants in their circular economy (CE) capabilities and the motivations driving such initiatives. Such a comparative study relies on a content analysis of sustainability and CE-related documents or reports, as well as results from four workshops conducted with five organisations. First, in response to the different types of CE capabilities observed in the organisations, a two-tiered categorisation of CDC beneficiaries is suggested: CE “operators” and “facilitators”. This categorisation is likely to influence the design of the CDC framework by highlighting the need to introduce a multi-scale perspective within the design of the CDC. Indeed, both facilitators and operators are interested in micro-level CE indicators for self-implementation of CE strategies within their organisations. However, only facilitators are also interested in meso and macro levels, reflecting their added focus on, amongst others, fostering networks and enabling collaboration between stakeholders (although, in some cases, operators can also be interested in meso-level indicators when they are part of eco-industrial parks). Second, analysing motivational factors for developing CE practices emphasises the importance of regulatory compliance. However, regulations mainly focus on the end-of-life and waste treatment aspects of CE, especially for public organisations such as local authorities. Two other main motivational factors are described: economic incentives (competitors' pressure, market share, profitability gains, etc.) and environmental objectives (compulsory and voluntary commitments). Therefore, the ambition behind circularity strategies is not solely centred on inherent circularity. There is a need to consider circularity as a means rather than an objective. These considerations advocate adopting a multi-criteria approach in the CDC framework, combining circularity metrics with economic and environmental performances. Moreover, this introduction of the concept of performance assessment raises the question of positioning results on a performance scale. Several options are possible through relative performance assessment (vs. past performance, vs. performance of similar players, etc.) and absolute performance assessment (vs. national, international, scientific framework, etc.). For the latter, it is possible to refer to a framework such as the planetary boundaries, which would also enable setting science-based objectives (cf. absolute environmental sustainability assessment methodology). To enrich the CDC conceptual framework, the categorisation of organisations needs to be further studied (beyond “operators” and “facilitators”), possibly through a persona-based design approach. Furthermore, the willingness and ability of the different types of organisations to adopt absolute sustainability approaches will be investigated through an interview campaign.