This research aims to investigate how Korean digital agencies practice design thinking for their website innovation. Based on a literature review on the design- thinking-driven web development process, multiple case studies of award-winning website projects were undertook. Through analyses of these cases, the following challenges and lessons were disclosed: (1) challenges – building a long-term, playful partnership with clients, leveraging decision-making executives’ design thinking awareness, and coping with limited resources (design thinking practitioners, budgets, and schedules) and (2) lessons – cross-functional collaboration, agile mobile-first development process, powerful visual storytelling, and compelling UX strategies and UI guidelines. Moreover, distinct approaches of design thinking practices were identified according to two website types: a brand promotion website – killer branding content-driven approach, and a service channel website – better UI/UXdriven approach.