As agile practices lack a focus on understanding the actual problem, and Design Thinking is assumed to be a promising approach to complement agile practices regarding this lack, this graduation project aims to identify opportunity areas to leverage the Design Thinking methodology in the process of agile software development. The context of focus was a specific technology unit within Nike, Inc. The main research question is formulated as follows: ‘How might we use Design Thinking to our advantage in the agile software development context of the targeted Nike Technology unit?’ Recognizing that Design Thinking is a contextual concept that needs further adaptation to contextual user needs, literature research and context analysis are done towards Design Thinking, agile software development, and related opportunities and boundaries. Research findings following the interviews indicate three main areas of concern that form boundaries to problem exploration: having a solution-oriented rather than a problem-oriented mindset, organizational structures that limit the space for problem exploration in terms of time, processes, and the role of technology in the problem exploration phase, and the need and importance of having a clear and aligned vision. Literature and exploratory research findings are integrated, answering the research question through a conceptual model covering three key principles: problem-oriented and human-centered thinking, dynamic alignment towards strategic fit, and divergent thinking to consider more fit-for-purpose alternatives. Subsequently, the conceptual model is translated into a usable artifact: a Problem Deep Dive Canvas accompanied by a Problem Deep Dive Tool Guide. The product aims to support product managers and product owners to put the key principles of the conceptual model into practice in collaboration with agile software development teams and business stakeholders. The threshold to use the product is low as there are no significant conflicts with current structures and processes. Initial validation results are promising towards feasibility, desirability, and viability of the product. Using the canvas on actual requests already showed that the outcomes of the canvas potentially significantly impact the further trajectory of the intended projects.