Several studies on digital servitization strategies highlight that their implementation is closely associated with some form of business model innovation. In order to engage in these innovation projects, firms need to expand their internal knowledge and skills while leveraging external organizations that support them in their servitization journey. To date, little is known about the intra-organizational factors accounting for the activation of new relationships with such knowledge-intensive service providers. This paper adopts a configurational approach for investigating the role of knowledge-intensive relationships in digital servitization strategies. Findings are founded on a multi-method investigation based on a structured survey and semi-structured interviews to Italian B2B manufacturers. The study contributes to the digital servitization literature showing the conditions that lead firms to develop relationships with different types of external providers of knowledge-intensive services, highlighting the role of firm’s size, digital readiness, internal commitment, and specific hiring programs in digital servitization paths.