Considerations for Migration to Headless CMS

A recruiter contacted me recently about a project migrating a B2B commerce implementation to headless CMS, which got me thinking about how I might approach such an opportunity.

When I walk into a relatively open engagement like this, I generally try to interview as many people as I can, whether I have a chance to prepare questions in advance. Here are some of the issues that I would hope to discuss, each of which is likely to lead to additional questions:

  • Describe the full scope of solutions to migrate.
  • What is the motivation for moving to headless?
  • Will the headless be SaaS, and does the organization have an overall goal of moving to SaaS? Without SaaS, it may not be possible to get the intended value from decoupling or a migration to headless (see
  • What are the platform and vendor (CMS) technologies in the existing solution?
  • What are some of the pain points with the existing solution?
  • With what systems does the existing solution integrate? Commerce typically implies at least authentication and search, if not experience management, and most solutions involve at least analytics. Do those systems provide the required integration points, such as webhooks, REST endpoints, use of message buses, and otherwise?
  • How significant is the existing codebase to migrate?
  • How extensively has the CMS been customized? Which of those customizations can be discarded?
  • What will be the new platform content delivery technologies?
  • What are the main requirements for the new CMS? If the organization has not selected a headless CMS, see
  • Describe existing and optimal development and deployment tools and processes.
  • Describe existing and optimal project management strategies, structures, and tools.
  • Describe projected timelines.

In my opinion, excluding migration of customizations, very little of this is specific to headless CMS. The bigger transition is to SaaS and hopefully MACH (microservice, (REST) API, cloud-native, headless) architectures in general.

If you would add considerations to this list, please comment on this blog post.

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