Have any of you deployed a headless content management system in your web / digital experience? What were the challenges you ran into?
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Headless CMS was a wise decision for flexibility. However, make sure you have a talented developer on staff who knows how to make the most of this future-proofing move. Otherwise, you're not using it to its fullest utility.
As far as some issues when we moved to headless: remaining on an existing account until you go live on headless (and remembering to close out prior account to avoid charges), having to create a separate account for the headless services, preparation for new firewall provider, which means site would be unavailable during the cutover, and general issues/costs with moving domains off legacy system into new server and firewall ecosystem.
Good luck!
In my experience, headless web architectures and CMS create extremely fast/responsive websites and when they leverage a CDN network to support fast delivery of content can really make or break an ecommerce site. They do require a coded website which is not easy to maintain by non-engineering resources. If your wireframe/design for each page is not changing but the images or information inside the frame changes than headless may work very well (for an example of a headless site see: Katespade.com
A headless system is just more flexible. It does not need to be complicated. For many, the fact a WCMS is headless should be transparent.
Headless just means separation from content management and presentation, which means you can present content in more ways, to more systems. Headless systems have been around for decades.