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This paper sets out with the premise that a Web designer's professional training and education can shape his problem-solving orientation and world view by indoctrinating certain values and conditioning him to think and behave in certain ways. By necessity, Web-based systems development teams are multidisciplinary, bringing together designers from a variety of different professional backgrounds such as graphic design, software engineering, HCI, and various others. A number of authors have suggested that it would be interesting to investigate methods and techniques used by Web-based systems designers from backgrounds other than computer-based systems development. However, this issue has received very little attention thus far. This paper makes a novel contribution by investigating this rarely explored gap in knowledge. Based on a qualitative grounded analysis of data gathered across 14 semi-structured interviews, four distinct orientations were identified: (1) Web development as the design of a functional software application (emphasis on back-end functionality); (2) as the design of an interactive tool (emphasis on ergonomics); (3) as the design of a communicational dialogue (emphasis on audience engagement); and (4) as an extension of branded graphic design (emphasis on visual presentation). The paper concludes with a call to broaden the traditional curriculum of systems analysis and design courses to encompass transdisciplinary concepts drawn from other complementary fields.