In recent decades, tech-companies such as Amazon, Google, Facebook, and Apple have grown exponentially, and it can be tempting for cities to try to attract these powerful corporations. This paper explores a particular aspect of this development, namely, how cities brand themselves to win the favor of a single big business. We draw on institutional isomorphism and a case study of North American cities’ branding efforts to attract Amazon’s second headquarters (dubbed HQ2). Our qualitative analysis shows that branding for a big business can lead cities into what we call sycomorphism, that is, acting obsequiously toward an important other in ways similar to other organizations. We identified three key expressions of sycomorphism: pandering, identification, and blank-checking. Our study contributes with knowledge that cities are not only subject to generalized pressure to compete for businesses, but they are also enticed by single powerful actors outside their organizational field, that can “jolt” cities to communicate obsequiously to win favor. Through the concept of sycomorphism, we advance the theoretical understanding of the relationship between isomorphism and city branding and thereby expand the usefulness of institutional theory in marketing scholarship.