A year ago, I’d have told you that APIs and automatic generation are oil and water. I’d spent too long stuck in a world where scalable API authoring came at the cost of a permanently sub-par developer experience. These days, I feel the exact opposite — APIs that use automatic generation the right way consistently win more developers.
In this talk I’ll share the journey that changed my mind — helping migrate the HelloSign public API to OpenAPI in early 2022. I’ll cover the challenges we ran into, discuss the tools we chose for generating documentation and SDKs, and we’ll explore the completed solution together. I’ll also talk about the initial goals of the project and impact we’ve observed since launch. You’ll leave with a deeper understanding of the OpenAPI spec and (hopefully) shared enthusiasm for using automatic generation to create truly delightful developer experiences for users of your public API.

I work on the "API Pod" at HelloSign (Dropbox) and own developer experience. In early 2022 we migrated to OpenAPI and use that to power our documentation and all our SDKs. This is one of a few talk ideas that explore the same topic from different lenses.