Have any of you deployed a headless content management system in your web / digital experience? What were the challenges you ran into?

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