Businesses are increasingly focussing their efforts on developing sustainable technological innovations. In doing so, they face obstacles in the systemic nature of innovation processes, the uncertain and ambiguous nature of sustainability, and in reconciling their business model and strategy with social and environmental value creation. This is particularly the case for those trying to emulate the so-called ‘Silicon Valley model’, which prioritises speed to deliver on its ambitious socially significant mission, relies on high-risk venture capital financing, and encourages flexibility and curiosity on the part of employees. This article uses data gathered during an action research case study to explore whether this much vaunted model could be better aligned with sustainable development. While, in this case, we find systemic and cognitive challenges to be currently precluding concerted action on sustainability, we also identify opportunities for greater alignment. Changes in the market and financial environment promise to provide new incentives for sustainability while the use of public deliberations such as citizen assemblies could help to reduce ambiguity. Complementary application of approaches like Constructive Sustainability Assessment within companies would allow business models to be more proactively and demonstrably aligned with employee values and ambitious sustainability missions.