We discovered the importance of content modeling when shifting from monolithic systems to extensible microservices like Contentful, where decoupled content makes it crucial to get the model right to speed development and minimize time to market. Our experience with monolithic systems taught us that a more focus on specific models instead of generic reusable ones is necessary, and we now emphasize an API-first approach in our digital experience stacks. A key consideration is the role of the customer in content modeling, as they often lack knowledge about considerations regarding content modeling, requiring guidance through the process. We use a "three phase approach" to design models in Contentful's web app, and explain the difference between page-oriented and content-oriented content models, which are independent of presentation, easily reusable, and channel-independent, or organized around a channel with flexibility for content managers.