Collaboration between designers and craftspeople, or designers and small manufacturers, is a strategy aiming to revive the local manufacturing industry in countries impacted by post-industrial economic challenges. In this paper we examine a local initiative-a community of practice (CoP) composed of designers and craftspeople-by studying how they have used technology to collaborate, in order to identify opportunities for long-term growth of this community. To gain a deep understanding of the dynamics in the community, the collaboration process during the workshop and after it, we used a three-phase qualitative research strategy. We conducted interviews with the participants and staff, analyzed an 11-month period of communications in the WhatsApp group and, finally, conducted a co-design session. We identify opportunities and challenges related to the design and implementation of a personalized collaborative system that fulfills the needs of the users as individuals and community members.