This research investigates how digital design agencies and client companies incorporate design thinking―a human-centered approach to solving difficult problems―into their website development processes. Based on a literature review on the design-thinking-driven web development process, multiple case studies of award-winning website projects were performed by in-depth interviews with key practitioners. Through analyses of these cases, their user-centered approaches for website innovation were identified according to the following four phases: web planning (discovery and defining phases) and web design and development (development and delivery phases). Moreover, distinct approaches of design thinking practices were identified according to two website types: a brand promotion website with a killer brand storytelling approach; and a service channel website with a strategic UI/UX-driven approach. Next, the key success drivers of these website projects were suggested in light of the typical themes of design thinking (i.e., human centeredness, research based, context awareness, and collaboration). Some practical limitations were also found in adopting the design-thinking-driven web development process, such as limited research methods and tools, and insufficient prototyping and experimentation. Along with these limitations, it was also discovered that current digital design agencies still face the following challenges in adopting the design-thinking-driven web development process: building a long-term, playful partnership with clients; leveraging decision-makers' design thinking awareness; and coping with limited resources (design thinking practitioners, budgets, and schedules).