GoKawiilAs I mentioned in my post earlier this week, we just completed a migration from WordPress to Jekyll. I outlined a couple of reasons for it but basically came down to preference, speed, and ability to make changes easily.
Frameworks like Jekyll (or Astro) aren’t for everybody, although they make a lot more sense in the general environment of AI proliferation, markdown becoming the lingua franca of LLMs, and a general trend toward headless sites. Everybody knows how insecure WordPress can be, although this is largely mitigated by working with a reputable host.
The biggest issue was speed. As a platform company, we move very fast and we always felt limited by what we could do with WordPress and we were constantly bottlenecked by whether or not we had WP developers available. But it’s hard to find good developers for any framework and especially for WordPress. When you find someone who is good at WordPress development, it means they are good at pretty much everything else they try and so it feels like a waste of talent to have them work on WordPress. It’s like a built-in brain drain.
Since the advent of coding agents like Claude Code, it has now become easier to completely route around this problem by simply migrating to another platform. We chose Jekyll for the reasons I’ll discuss in the next section.
Architecture decisions that led to Jekyll
Just last week, Cloudflare announced a new CMS framework that they have dubbed the “spiritual successor” to WordPress. It’s based on Astro, which is one of the most popular static site generators (SSG) right now. It looks great, but we wanted something that we had experience with and was a mature framework. As I mentioned in my previous post, our site ran on Jekyll long ago so we knew it well.
For those who are not familiar: the biggest difference between a CMS like WordPress and an SSG is that there is no database (typically), nor even an application server in the latter. You’re working entirely in HTML templates, includes, layout files, config files, and then markdown for everything else.
Metadata on the page is defined as frontmatter, which is the YAML data between the --- delimiters at the top of the markdown file.
So, for example, the frontmatter for this post looks like this:
layout : post title : " Moving from WordPress to Jekyll (and static site generators in general)" description : " Some technical notes on how and why we moved from WordPress to Jekyll, a well-known static site generator (SSG)." date : 2026-04-09 author : Ray Grieselhuber permalink : /blog/rebuilding-demandsphere-with-jekyll-and-claude-code/ tags : - Engineering - AI Search
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