Closing a Chapter at Automattic  🔗 **Source:** [Closing a Chapter at Automattic](https://j.cv/closing-a-chapter/) > [!note]+ Document Notes > ```yaml > > --- > tags: [WordPress, Automattic, AI] > author: [MISSING] > source: j.cv > reference: [https://j.cv/closing-a-chapter/] > date created: 2026-05-19 00:00 > > --- > ``` > # 🏷️ Title: Closing a chapter at Automattic <!-- deep-read:sections start --> ## 🧭 Table of Contents - [📝 Summary](#-summary) - [📖 Main Content](#-main-content) - [🗒️ Notes](#️-notes) - [📚 References](#-references) - [🗣️ Paraphrase](#️-paraphrase) - [📰 Newsletter](#-newsletter) - [✅ Action Items](#-action-items) - [🧪 Hypotheses](#-hypotheses) - [📊 Methodology](#-methodology) - [❓ Questions](#-questions) - [🔮 Future Research](#-future-research) - [💡 Implications](#-implications) - [🧠 Learning Styles Assessment](#-learning-styles-assessment) - [📊 Accessibility Assessment](#-accessibility-assessment) - [🌍 DEIB Assessment](#-deib-assessment) - [✅ Logical Validity](#-logical-validity) - [🛡️ DARVO Analysis](#-darvo-analysis) - [🎯 Conclusion](#-conclusion) ### 🔗 References - Include links cited in or relevant to the article. --- ## 📝 Summary - What happened: The author is leaving Automattic as Head of AI and Core AI lead for WordPress after ~18 months since the WPAI acquisition, moving to a new AI venture. - Why it matters: Marks a leadership transition for Core AI and a phase change in how WordPress/Automattic approach AI, the “Agentic Web,” and open web foundations. - Key stakeholders: Automattic, WordPress Core AI contributors, wider WordPress community, WooCommerce/WordPress.com customers, future AI startup collaborators. - Risks and tradeoffs: Leadership change risk for Core AI; opportunity cost of losing a key coordinator vs. fresh leadership and focus for the author’s new work. - Bottom line: Core AI and Automattic are positioned strongly; the author steps into a new AI research/build role while remaining close in an advisory capacity. --- ## 📖 Main Content - The author announces their last day at Automattic and as Core AI lead for WordPress, noting how rapid the journey since the [WPAI acquisition](https://techcrunch.com/2024/12/09/automattic-acquires-wpai-a-startup-that-creates-ai-solutions-for-wordpress/) has been. - They recount forming Core AI, building the [AI Building Blocks](https://make.wordpress.org/ai/2025/07/17/ai-building-blocks/), and shipping the last one in WordPress 7.0, with thousands of commits and stars from contributors, and #core-ai Slack scaling from 0 to 1000+ people ([overview of this phase](https://read.readwise.io/read/01krxykq678fz1xn85jn881bwq?endLexposition=00000_00000_00007_00007_00001_00000-000K&emphasizeText=We+formed+Core+AI%2C+then+built+the+AI+Building+Blocks&startLexposition=00000_00000_00001)). - Automattic’s AI work included AI website builders, agents, code editors, agentic commerce, conversational analytics, MCPs, and more, with AI staff growing from ~10 to ~70, reflecting a rapid build-out of an AI division. - The author expresses gratitude to leadership, teams, contributors, and mentors, emphasizing the collaborative nature of the work and the scale at which they could learn and lead ([thank‑you passage](https://read.readwise.io/read/01krxykq678fz1xn85jn881bwq?endLexposition=00000_00000_0000B_0000A-000M&emphasizeText=I%E2%80%99d+like+to+say+thank+you+%E2%80%93+to+so+many+folks&startLexposition=00000_00000_00007_00009)). - They articulate a thesis: in an era where “code is effectively free,” brand, legacy, taste, and distribution matter more, and defending the Open Web while building the “Agentic Web” is vital. They see Automattic and WordPress as uniquely well‑positioned to do this. - The author stresses that WordPress as a project is an essential foundation for an open, decentralized internet; Core AI work has helped ensure it can remain that foundation and help democratize publishing and “representation” in the AI era ([open web argument](https://read.readwise.io/read/01krxykq678fz1xn85jn881bwq?endLexposition=00000_00000_0000K&emphasizeText=It%E2%80%99s+essential+that+it+remains+the+foundation+of+an+open%2C+decentralized+internet&startLexposition=00000_00000_0000D)). - They will stay close to WordPress in an advisory role but see this as a clean chapter closing; their day‑to‑day will shift fully to a new project. - The “what’s next” section hints at work on complex systems, foundational models, time, and “true AI research,” assembling an in‑person, “avengers‑level” team in NYC/Boston, with more details to be shared later. --- ### 🗒️ Notes - Announcement: “Today is my last day at Automattic as Head of AI, and my last day as Core AI lead for the WordPress project.” This frames the piece as a transition note. - Timeline: Since the acquisition of WPAI, only ~18 months have passed, underscoring the speed of change and delivery. - Core AI formation: Core AI was created, and AI Building Blocks were delivered, culminating in the final block shipping with WordPress 7.0 ([Core AI recap](https://read.readwise.io/read/01krxykq678fz1xn85jn881bwq?endLexposition=00000_00000_00007_00007_00001_00000-000K&emphasizeText=We+formed+Core+AI%2C+then+built+the+AI+Building+Blocks&startLexposition=00000_00000_00001)). - Community scale: #core-ai Slack grew from 0 to 1,000+ people; contributor day tables overflowed; ~3,942+ commits and ~2,330+ stars were counted (calculated using Claude). - Product outputs: AI website builders, built‑in agents, AI‑enabled code editors, “agentic commerce support,” and conversational analytics for major publishers, plus support for MCP‑style integrations. - Org growth: AI teams scaled from ~10 people on a few projects to ~70 working on interconnected AI initiatives. - Emotional tone: The author emphasizes “incredible pace” and “talented people,” describing it as a privilege to work both async and in offices (NYC, SF). - Gratitude: They thank leadership, teams, contributors, mentors, and those who will continue “to garden what we’ve helped seed and grow,” indicating continuity beyond their tenure ([gratitude section](https://read.readwise.io/read/01krxykq678fz1xn85jn881bwq?endLexposition=00000_00000_0000B_0000A-000M&emphasizeText=I%E2%80%99d+like+to+say+thank+you+%E2%80%93+to+so+many+folks&startLexposition=00000_00000_00007_00009)). - Strategic thesis: In the memo, the author argues that in an era where “code is effectively free,” four attributes dominate: good brand, legacy, taste, and distribution. Automattic is presented as strong on all four. - Open Web + Agentic Web: There is a “real reason to defend the concept of the Open Web, while building what’s next – which to me, is the Agentic Web,” referencing broader thinking and a WCAsia keynote. - WordPress as foundation: WordPress is framed not just as a CMS but as infrastructure for an “open, decentralized internet.” Core AI work is seen as helping to keep it that way in the AI era ([open web and Core AI](https://read.readwise.io/read/01krxykq678fz1xn85jn881bwq?endLexposition=00000_00000_0000K&emphasizeText=It%E2%80%99s+essential+that+it+remains+the+foundation+of+an+open%2C+decentralized+internet&startLexposition=00000_00000_0000D)). - Democratizing publishing and representation: The mission expands from “democratizing publishing” to “democratizing publishing (and now, representation too)” in an AI context—hinting at representational fairness and inclusion in AI systems. - Role shift: The author will remain an advisor but sees this as a “closing chapter” for their day‑to‑day WordPress involvement. - New venture: They are forming an in‑person team in NYC/Boston, working on complex systems, foundational models, time, and “true AI research,” inviting interested readers to reach out and watch their Twitter for updates. --- ## 📚 References - [Closing a chapter at Automattic](https://j.cv/closing-a-chapter/) - [Leadership transition for the Core AI team](https://make.wordpress.org/ai/2026/05/18/leadership-transition-for-the-core-ai-team/) - [Automattic acquires WPAI](https://techcrunch.com/2024/12/09/automattic-acquires-wpai-a-startup-that-creates-ai-solutions-for-wordpress/) - [AI Building Blocks announcement](https://make.wordpress.org/ai/2025/07/17/ai-building-blocks/) - [Automattic AI 2025 retrospective/thinking](https://j.cv/automattic-ai-2025/) - [WordPress.com AI site builder coverage](https://www.t <!-- deep-read:sections end --> 📄 **Full text:** ![[Full Document Contents/Articles/Closing a Chapter at Automattic.md|Closing a Chapter at Automattic by .Wp-Block-Comment-Author-Name Box-Sizing Border-Box & Sourceurl Https & J.Cv Wp-Content Plugins Gute...]] ## Highlights - I’d like to say thank you – to so many folks, it would be impossible to list them here. Leadership for the opportunity to learn and lead at scale myself. Our teams in Automattic, and contributors in the project for the trust in me, and the support and enthusiasm of our work, despite a lot of unknowns and continual change. My mentors and friends, Matias, Matt, Rich, Jason, and many more for the guidance and advice. And for those that will continue to garden what we’ve helped seed and grow. ([View Highlight](https://read.readwise.io/read/01ks00496kbd59jxpvh9m4nj5e)) - Tags: 👻 ai highlighted