Sketching for conceptual design has traditionally been performed on paper. Recent computational tools for conceptual design have leveraged the availability of hand-held computing devices and web-based collaborative platforms. Further, digital sketching interfaces have the added advantages of storage, duplication, and sharing on the web. We have developed skWiki, a tool that enables collaborative sketching on digital tablets using a web-based framework. We evaluate skWiki in two contexts, (a) as a collaborative ideation tool, and (b) as a design research tool. For this evaluation, we perform a longitudinal study of an undergraduate design team that used skWiki over the course of the concept generation and development phase of their course project. Our analysis of the team’s sketching activity indicated instances of lateral and vertical transformation between participants, indicating collaborative exploration of the breadth and depth of the design space. Using skWiki for this evaluation also demonstrated it to be an effective research tool to investigate such collaborative design processes.