Critical thinking is considered one of the most significant competencies that employees need to develop in order for them to contribute to an organisation’s success and productivity. The lack of professional development opportunities aimed at enhancing the critical thinking capacity of employees might be deleterious for organisations seeking to capitalise on this competence as a means of remaining innovative. By means of a conceptual case study of Thinkerly – a business-to-business (B2B) firm offering critical thinking training solutions in Malta – this article considers the firm’s business idea, target customer segment, and competitive external business environment. The hypothetical business proposal analyses the internal and external factors affecting the firm’s performance and evaluates the positioning, strategy and competitive advantage of the bespoke training firm. The primary objective of the conceptual case study is to indicate the main considerations a B2B company needs to take when developing critical thinking training in a specific context. To illustrate how any such proposal is likely to have its limitations, two of the models utilised in the design of Thinkerly’s proposal are subjected to critique.