Artificial Intelligence


  • Two Weeks at AI Enablement, NYC 

    Last month I spent two weeks with Cohort 3 of Automattic’s AI Enablement program: fifty Automatticians from product, design, engineering, data, and ops, sharing one room in New York. Notes from the cohort: how we learned from each other, the patterns in everyone’s AI workflows, and three things I built.

  • Move Fast and Don’t Break Things: Shipping the Simplenote MCP

    When Automattic recently launched a month‑long hackathon, engineers Mark Biek and Evan Tobiesen knew exactly what they wanted to work on: the Simplenote Model Context Protocol (MCP) server. Neither Mark nor Evan works in data science, so measurement might have been the easy thing to skip. Instead, they shipped a product with built‑in measurement from…

  • From Messages to Episodes: Building Better Recall for AI Support

    Our customers do not think of support as isolated chats. They think in terms of things they are trying to get done: connecting a domain, changing the look of a site, launching a store, fixing checkout, recovering access, or understanding a bill. That creates a challenge for an AI support assistant. If a customer returns and says: Let’s…

  • From Default to Delightful: AI-Assisted Data Visualization

    I can never remember the exact syntax for visualization libraries. AI changes this. Now I describe what I want in natural language, iterate in conversation, and let the model handle the boilerplate. Five prompts transformed default charts into a visual story of WordPress’s 20-year evolution.