This project tackled two research questions for separate clients. The first question was posed by Livework, a service design agency, which wanted to learn how systemic design principles can be applied in projects aimed at organisational sustainability transformations. The second client, Juvenile Company, a company that designs and manufactures strollers and other juvenile products, wanted to figure out what their relationship with customers and business partners should look like to reach their sustainability goals by 2035. Through a series of analyses and co-creative design activities, I discovered two key factors that might serve as an opportunity or barrier in Juvenile Company’s transition towards a more sustainable future: the relationship between parent and stroller in the current system and Juvenile Company’s culture of product innovation through design. Using context mapping, insight into the value exchanges between parent and stroller over time were captured. This led to identifying three distinct phases of value creation tied to a child’s developmental stages. It was found that the value implicitly delivered by the stroller over these developmental stages is the core value proposition of Juvenile Company. It was found that Juvenile Company’s current strategy of revenue growth through product innovation is at odds with its sustainability goals. To achieve its sustainability goals, Juvenile Company must rely on qualitative innovation, rather than quantitative, to drive revenue growth. Using the input from all research, a vision statement was formulated that describes the possibility space of Juvenile Company’s future innovation. “Juvenile Company empowers parents and their children to explore the world by providing value beyond products that adapts to parents’ changing needs without compromising the future needs of their children.” A design strategy concept was created to describe what a circular Juvenile Company will need to look like to be fully circular. The concept consists of four elements that build on one another. At the deepest layer sits a new mental model: a culture of innovation through qualitative value creation. To create qualitative value, on the next layer up we find a reframed version of the core value proposition discovered through the context mapping research. Juvenile Company focuses on developing value explicitly for the three developmental stages identified. To guide the development of this value, three core vision principles were developed: Value beyond products, Adapting to changing needs and Dependable guide. To further illustrate these vision principles, thirteen key propositions were designed that help shape what the relationship between parents and Juvenile Company could look like in the future. This strategy was conceptualised through two deliverables: a parent-Juvenile Company relationship journey map that describes how the key elements to the relationship interlink, and a children’s book that describes the story of how one family’s relationship with Juvenile Company develops over time. Through constant reflection over the course of this process, key insight was created into how Livework designers can implement systemic design principles in organisational sustainability transformation projects. A knowledge gap was identified, consisting of three layers that each describe a different type of knowledge Livework designers must acquire. Additionally, it was found that a major difficulty in applying systemic design principles will be adopting an ecosystemic design lens that focuses equally on human and non-human participants of a system. Further implications and opportunities were identified that might shape how Livework approaches design projects.