Business model innovation (BMI) and organizational ambidexterity have been pointed out as mechanisms for companies achieving sustainability. However, especially considering small and medium enterprises (SMEs), there is a lack of studies demonstrating how to combine these mechanisms. Tackling such a gap, this study seeks to understand how SMEs can ambidextrously manage BMI. Our aim is to provide a practical artifact, accessible to SMEs, to operationalize BMI through organizational ambidexterity. To this end, we conducted our study under the design science research to, first, build an artifact for operationalizing contextual ambidexterity for business model innovation. Then, we used an in-depth case study with a vegan fashion small e-commerce to evaluate the practical outcomes of the artifact. Our findings show that the company improves its business model while, at the same time, designs a new business model and monetizes it. Thus, our approach was able to take the first steps in the direction of operationalizing contextual ambidexterity for business model innovation in small and medium enterprises, democratizing the concept. We contribute to theory by connecting different literature strands and to practice by creating an artifact to assist management.Sustainability 2020, 12, 2337 2 of 34 pressure from economic, social and environmental demands, entailed by the transition to sustainable development (SD) [14]. Incorporating environmental and social aspects into businesses represent additional challenges for BMI processes. It requires cross-functional and systems thinking, as well as radical changes in business processes, products, and organizational forms [15]. As a result, most BMIs for sustainability are developed ad-hoc and are neither systematic nor systemic [16].Thus, there is a need to exploit established BMs and, at the same time, a need to search for new BMs that adapt to the needs and demands that are constantly changing, in order to become a sustainable organization, that is, an organization that can achieve (enduring) success while performing well in economic, social and environmental aspects. This managerial capability to exploit and explore refers to organizational ambidexterity [17,18]. Organizational ambidexterity has also been often highlighted as a mechanism to attain sustainability [19,20]. However, this is another concept that is difficult to implement [21]. Again, in the context of SMEs, it becomes an even more difficult task [12], even though, as suggested by recent studies, SMEs could benefit from being ambidextrous and should take action in this direction [22].It is observed that, although BMI and ambidexterity are important mechanisms for achieving sustainability, the connection between both concepts has received limited attention in the literature [23]. This gap is even larger from the perspective of SMEs, as BMI literature mostly focuses on large companies, often neglecting SMEs [7,24]. Laudien and Daxböck [4] argue that BMI research should go beyond the focus on large, established compani...