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 > ## 🧭 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 Today is my last day at Automattic as Head of AI, and my [last day](https://make.wordpress.org/ai/2026/05/18/leadership-transition-for-the-core-ai-team/) as Core AI lead for the WordPress project. Since the [WPAI acquisition](https://techcrunch.com/2024/12/09/automattic-acquires-wpai-a-startup-that-creates-ai-solutions-for-wordpress/), it’s been an incredible ride and shocking to think that it’s been only a year and a half. *(And if you’re here because you heard I’m building something new – skip to the bottom for a sneak peek.)* So much has happened [in Automattic](https://j.cv/automattic-ai-2025/) and WordPress since. We formed Core AI, then built the [AI Building Blocks](https://make.wordpress.org/ai/2025/07/17/ai-building-blocks/), the last of which ships in WordPress 7.0. #core-ai’s Slack went from 0 to 1,000+ people, contributor day tables were overflowing, and ~3,942+ commits / ~2,330+ stars (real numbers calculated by Claude) were made to the AI work for WordPress. At Automattic, we released [AI website builders,](https://www.theverge.com/news/645993/wordpress-com-is-offering-a-new-ai-site-builder) [built-in agents,](https://theaiinsider.tech/2026/03/21/wordpress-com-introduces-ai-agents-to-automate-website-creation-and-management/) [code editors](https://techcrunch.com/2025/12/03/wordpresss-vibe-coding-experiment-telex-has-already-been-put-to-real-world-use/), [agentic commerce support,](https://www.searchenginejournal.com/woocommerce-is-integrating-agentic-ai-capabilities/563226/) [conversational analytics for the largest publishers on the internet](https://wpvip.com/blog/parsely-sage-ai-editorial-intelligence/), [MCPs](https://pressable.com/knowledgebase/get-started-with-wordpress-mcp-on-pressable/)… the list can go on. Our teams went from ~10 folks working on a few projects when I joined to ~70 building impressive, interconnected work all in tandem. The incredible pace and the talented people that made it happen were a privilege to get to work with each day – be it async, or from the NYC (and SF) office. STOW 2025 WCAsia Keynote AI Division Meetup WCUS Contributor Day Architecture Leadership Meetup WCUS Panel The SF Office Woo Partner Day 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. I wrote in an internal memo; the company has an incredible future ahead of it. In my opinion, (good) brand, legacy, [taste](https://j.cv/craft-code-art/) and distribution matter more in an era when code is effectively free, and there’s a real reason to defend the concept of the Open Web, while building what’s next – which to me, is the *Agentic* Web. [There’s a lot of thinking on this concept here on the blog](https://j.cv/agents-the-new-internet-3-5/), and I’m really glad I had the chance to really crystallize that in this year’s [WCAsia Keynote](https://j.cv/wcasia-2026-opening-keynote/). Automattic has all four of those qualities on display and there’s no better group than those that I’ve worked with during my tenure to build what the internet should become (and the ongoing [Radical Speed Month](https://www.linkedin.com/posts/automattic_radicalspeedmonth-activity-7453472838973317120-DEfh/) deliveries prove it). And, while this sentiment absolutely aligns with Company and our great products over at [WordPress.com](https://WordPress.com) and [WooCommerce](https://WooCommerce.com) (for those out of the industry; Automattic’s hosting for the foundation of the internet, and the second largest ecommerce platform, after Shopify), it’s almost *more* applicable to the WordPress project in general. We have something special, and important. It’s essential that it remains the foundation of an open, decentralized internet – and I think the work we’ve done in Core AI has put us in a position to keep building towards that goal of democratizing publishing (and now, representation too) in this new AI era. I’m excited to remain close to this work and mission in an advisory role, but at the same time, see this as a closing chapter. For my true day-to-day, I will transition out of WordPress to deeply focus on something new. What’s next really excites me, and I’m getting started right away with an immensely talented group of folks pursuing some really big, hard and impactful problems. I’ll get into what we’re working on in a future post, but if complex systems, foundational models, time 🦋, true AI research, and applications of it in the real world excite you, [please do reach out](mailto:[email protected]). We’re assembling an avengers-level in person team based in NYC and Boston. You’ll hear all about it on my [Twitter](https://x.com/jameswlepage) soon 🙂, Closing a Chapter at Automattic, .Wp-Block-Comment-Author-Name Box-Sizing Border-Box & Sourceurl Https & J.Cv Wp-Content Plugins Gute..., 01krxykq678fz1xn85jn881bwq.