Explore every episode of the podcast Headless

The CMS is having an identity crisis.

Salesforce is buying Contentful. Cloudflare built an AI-native “spiritual successor to WordPress.” Drupal believes its famously intense governance model may be exactly what AI agents need. Meanwhile, WordPress sites are being recruited into global cybercrime operations while Automattic and WP Engine continue turning open-source governance into prestige television.

Hayden also returns to the comments section, where one AI agent broke 18 Webflow blog posts, a photographer built his own CMS out of spite, and a Reddit user explained why self-discoverable APIs may finally get their moment.

This week on Headless:

• Why content is becoming infrastructure for AI
• Whether agents need a new kind of CMS
• How Drupal became Batman with a spreadsheet
• Why abandoned WordPress sites still matter
• Whether the CMS is dying or simply disappearing into the walls

Follow Headless for weekly CMS, DXP, AI, and web infrastructure news without the vendor-approved personality transplant.

Have a take, correction, confession, or deeply unhinged CMS story? Send it Hayden’s way. The comments section is officially part of the show.

Your CMS has a new user.

And it’s not human.

This week on Headless, we’re connecting a handful of stories that look unrelated until you zoom out.

WordPress 7.1 just shipped. Storyblok plugged directly into Claude. Optimizely fixed an AI agent that could accidentally wipe a page while confidently telling you everything went great. Salesforce is expanding something literally called “Headless 360.” And Contentful is asking a wonderfully ominous question: What if your next visitor isn’t a person?

Individually, they’re product updates.

Together, they point toward something much bigger.

The CMS is evolving from software humans use to infrastructure AI uses.

We break down what that means for WordPress, headless CMS, DXP, MCP, AI agents, structured content, governance, and the increasingly important question of whether the future of “headless” has anything to do with websites at all.

Plus: why Agent Experience might become the next battleground for CMS vendors, why boring things like metadata and permissions are suddenly very sexy, and one prediction about what every enterprise CMS RFP is going to include within the next 18 months.

Stories from this episode:

WordPress 7.1 “Mary Lou”
Released August 19 with responsive styling, collaboration improvements, media upgrades, new APIs, and more.
https://wordpress.org/news/2026/08/mary-lou/

Storyblok joins Claude’s Connector Directory
Storyblok can now connect directly to Claude through a remote MCP server with OAuth-scoped access.
https://www.storyblok.com/mp/storyblok-on-claude-connector-directory

Optimizely CMS 13 + Opal updates
Including the extremely important fix where an AI-powered CMS tool could empty a Visual Builder page and still report success. Computers remain undefeated.
https://support.optimizely.com/hc/en-us/articles/44937048830221-2026-Optimizely-CMS-13-release-notes

Salesforce expands Headless 360
Salesforce is turning capabilities across its platform into services that authorized AI agents can discover and use through open standards like MCP.
https://www.salesforce.com/news/stories/expanding-headless-360-enterprise-capabilities/

Contentful: “What if your next visitor isn’t a person?”
Contentful and Apply Digital dig into AI agents, discovery, and what it means to make content understandable to machines.
https://www.contentful.com/events/agentic-shift-website/

Headless is a weekly look at what’s happening across CMS, DXP, composable architecture, content infrastructure, and the increasingly weird future of the web.

Not just what happened.

Why it matters.