Agentic Website Conversion
The push to rebuild my site on GitHub Pages started as a practical alternative to Squarespace, but it quickly became a project about creative freedom. Running everything out of this repository means I finally have a transparent system where every page, asset, and layout is visible, versioned, and easy to change. The contrast with my old Squarespace setup is night and day: instead of feeling boxed in by their editor, I now have full ownership over the content I have been paying them to host for years.
The old Squarespace setup
The new GitHub Pages build
The real breakthrough, though, is how well this new setup works with agents. By “agent” I mean tools like Codex CLI, Codex Web, Claude Code CLI, or Cursor that let you direct an AI to edit the repo. Because the whole site lives in code, I can ask an agent to tweak the style of a section, rewrite copy, or automate the repetitive parts of publishing without worrying about a rigid UI fighting me. Delegating the tedious bits of documentation to an agent keeps my momentum up, and lets me focus on the creative decisions that actually matter.
The Migration Workflow
The conversion involved scraping 59 dev log entries, 5 talks, and 8 major experience pages from Squarespace. Rather than manually copying each one, we developed a workflow that an agent could execute:
# Fetch the rendered HTML
curl -sS "https://blog.drewskillman.com/experiences/<slug>" \
-o reference/<slug>.html
# Download media from the CDN
curl -sS "https://images.squarespace-cdn.com/content/..." \
-o assets/images/<slug>/image.jpg
# Create the Jekyll collection entry
cat > _experiences/<slug>.md
The agent would parse the saved HTML, extract text blocks and image URLs, download all media to assets/images/<slug>/, and generate the corresponding markdown file with proper frontmatter. What would have taken days of tedious copy-paste became a systematic process I could review and refine. It took about 4 hours to complete, a lot of which was me just keeping an eye on the agent as it worked and making sure I didn’t get screwed by any weird prompt injections. That part of a workflow like this is still a bit unnerving.
Under the old squarespace workflow, I would have skipped documenting this entirely. Now it is a lightweight task that fits into the cracks of my day.