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.theverge.com/news/645993/wordpress-com-is-offering-a-new-ai-site-builder) - [WordPress.com AI agents coverage](https://theaiinsider.tech/2026/03/21/wordpress-com-introduces-ai-agents-to-automate-website-creation-and-management/) - [WordPress “Telex” AI coding experiment](https://techcrunch.com/2025/12/03/wordpresss-vibe-coding-experiment-telex-has-already-been-put-to-real-world-use/) - [WooCommerce agentic AI support](https://www.searchenginejournal.com/woocommerce-is-integrating-agentic-ai-capabilities/563226/) - [Parse.ly / WPVIP Sage AI editorial tools](https://wpvip.com/blog/parsely-sage-ai-editorial-intelligence/) - [WordPress MCP overview](https://pressable.com/knowledgebase/get-started-with-wordpress-mcp-on-pressable/) --- ## 🗣️ Paraphrase - Paragraph A: The author is officially ending their roles as Head of AI at Automattic and Core AI lead for WordPress, reflecting on an intense 18‑month period since Automattic bought WPAI, full of rapid developments. - Paragraph B: They describe the growth and outputs of Core AI and Automattic’s AI teams, thank colleagues and mentors, argue that brand/legacy/taste/distribution matter most in a “code is free” world, link that to defending the Open and Agentic Web with WordPress as a foundation, note their shift into advisory status, and hint at a new, ambitious AI research venture. --- ## 📰 Newsletter Hey WordPress folks, Big leadership news in the AI space: the outgoing Head of AI at Automattic just published “Closing a chapter at Automattic,” reflecting on Core AI’s trajectory—from AI Building Blocks in WordPress 7.0 to agents, AI editors, WooCommerce agentic support, and more. It’s also a love letter to the Open Web and a teaser for a new agentic‑web‑aligned AI venture. Worth a read if you care about where WordPress AI goes next and how core, Woo, and .com fit together. For more background, check out the Core AI [AI Building Blocks explainer](https://make.wordpress.org/ai/2025/07/17/ai-building-blocks/) and the leadership transition note on [make/AI](https://make.wordpress.org/ai/2026/05/18/leadership-transition-for-the-core-ai-team/). --- ## ✅ Action Items #### DevRel - Map Core AI features (AI Building Blocks, agents, AI site builder) into sample projects, talks, and live demos targeted at plugin/theme authors. - Create a workshop series and office hours on “Agentic Web patterns in WordPress,” aligned with the author’s conceptual framing. - Improve AI docs: end‑to‑end examples, SDK patterns, and quickstarts for integrating with MCPs and Automattic AI endpoints. - Publish narrative posts and case studies on how Core AI aids large publishers and Woo stores; track engagement and contribution funnels. - Facilitate cross‑team AMAs (Core, Woo, WP.com, VIP) about AI roadmaps, including post‑transition plans for Core AI leadership. #### OSPO - Formalize AI‑related contribution policies and governance charters, clarifying how Core AI decisions are made post‑transition. - Review license compliance for AI integrations, model weights, and third‑party services used in WordPress.org and Automattic products. - Maintain a security intake for AI features (prompt injection, data leakage) and define embargo and disclosure processes. - Track AI‑related components in SBOMs for WordPress, Woo, and major plugins; set update and freshness SLOs. - Offer consult hours to plugin authors exploring AI features (legal, privacy, data residency, model terms). - Align AI roadmap KPIs with open web principles (e.g., local inference, self‑hosting options, interoperability requirements). #### Community - Maintainers: hold governance clinics on how AI issues fit into triage, release planning, and long‑term support. - Contributors: build AI “first‑issue” rotations and pairing sessions to bring more devs into Core AI components. - Sponsors: document funding needs for AI infra, evaluation, and safety work; publish impact reports tied to open web outcomes. - Ecosystem: run joint incident exercises (e.g., AI‑powered spam, content poisoning) across hosting, plugins, and core teams. #### WordPress - Core: clarify AI‑related priorities for upcoming releases post‑WordPress 7.0; ensure regression controls for AI‑powered features. - Core Performance: benchmark AI‑assisted flows (site creation, editing) and set budgets for latency and resource use. - Core AI: codify responsible AI guidelines, evaluation sets, and red‑team exercises; publish them on make/AI. - Core Program Team: ensure AI initiatives are integrated into release rhythms, cross‑team dependencies, and retrospective processes. - Mobile: explore how AI agents and building blocks surface in mobile site editing and content workflows. - Playground: provide AI‑ready blueprints/labs so devs can experiment with AI features without real data. - Community: add AI session kits and demo scripts to meetup/WordCamp resources. - Training: create Learn WordPress courses on AI Building Blocks and agentic patterns. - Marketing: align messaging about “Agentic Web” and AI with open web and decentralization narratives. - Support: update KBs and playbooks for AI‑driven features and failure modes (e.g., hallucinations, mis‑edits). - Design: run UX audits on AI features (discoverability, control, reversibility). - Documentation: keep DevHub/HelpHub in sync with Core AI APIs and user‑facing features. - Photos / TV / Polyglots / Accessibility / Meta / CLI / Hosting / Tide / Openverse / Themes / Plugins: - Integrate AI enhancements (e.g., captions, translations, accessibility checks, search) while enforcing open‑web, privacy, and provenance constraints. #### The WPOCC - Design fellowship tracks for AI maintainers, especially around Core AI, performance, and safety. - Fund documentation and governance sprints focused on AI and the Agentic Web. - Pilot small grants for model evaluation, open datasets, and reference implementations. ### FAIR - Ensure AI components in WordPress maintain technical independence (local metadata, provenance, signatures). - Document funding transparency, governance covenants, and anti‑capture safeguards for AI infra. - Package AI decision frameworks (charters, operator agreements) as reusable governance artifacts. --- ## 🧪 Hypotheses - H1: Clear governance and leadership continuity for Core AI will sustain or increase AI‑related contributions despite leadership change. - H2: Positioning WordPress as infrastructure for the “Agentic Web” increases long‑term community and ecosystem engagement. - H3: Emphasizing brand, legacy, taste, and distribution (over raw code) improves adoption of WordPress AI features. - H4: Advisory involvement from outgoing leaders mitigates disruption to AI roadmaps. --- ### 📊 Methodology - For H1: Pre/post analysis of AI‑related commits, contributors, and issue closure rates around the leadership transition. - For H2: Survey community sentiment and track growth in projects adopting agentic‑pattern features. - For H3: A/B test messaging emphasizing open web + brand/taste vs. purely technical AI capabilities, measuring adoption. - For H4: Compare roadmap slippage and launch quality between AI components with advisory continuity and those without. --- ### ❓ Questions - How will Core AI governance adapt after this transition? - What concrete commitments anchor WordPress as core infrastructure for the Agentic Web? - How can the community influence AI evaluation datasets and safety constraints? - Where will the boundary lie between Automattic’s commercial AI offerings and community‑owned AI infra? --- ### 🔮 Future Research - Formalizing “Agentic Web” architectures in the WordPress ecosystem. - Governance models for AI features in large open‑source projects. - Metrics for “representation” in AI‑augmented publishing tools. - Playbooks for leadership transitions in critical technical teams (like Core AI). --- ### 💡 Implications - Practice: Plugin and theme authors should design AI features that respect open web values and user agency. - Policy: WordPress governance bodies will need AI‑aware policies on privacy, safety, and content provenance. - Security: AI expands the attack surface (prompt injection, data exfiltration); shared mitigations are needed. - Education: The community must upskill around AI concepts, from basic usage to evaluation and ethics. - Funding: Sustained backing is required for open AI infra and governance, not just shiny features. --- ### 🧠 Learning Styles Assessment - Reading level estimate: Flesch‑Kincaid Grade roughly ~10–11 (assumption: long sentences, technical vocabulary). #### 👀 Visual learners - Present: Some implied slides/keynotes (WCAsia), but the blog post is text‑only. - Improve: Add diagrams of Core AI architecture, timelines of AI milestones, and screenshots of AI Building Blocks. #### 🔊 Aural learners - Present: None indicated. - Improve: Provide an audio read‑through or podcast‑style reflection on this “closing chapter.” #### 🗣️ Verbal learners - Present: Strong narrative, clear concepts like “Agentic Web,” and explicit framing (“code is effectively free”). - Improve: Add a short glossary for terms like “agentic commerce,” “MCPs,” “Core AI.” #### 🧩 Kinesthetic learners - Present: Indirect; references to tools that users can try, but no step‑by‑step tasks here. - Improve: Link to hands‑on tutorials for AI Building Blocks and agents. #### 🧠 Logical learners - Present: Clear causal narrative (acquisition → Core AI → products → future mission). - Improve: Include structured roadmaps, decision matrices for AI features vs. open‑web considerations. #### 🧑‍🤝‍🧑 Social learners - Present: Strong community framing (Slack growth, contributor days, meetups). - Improve: Add prompts for discussion at meetups/WordCamps, plus links to relevant channels. #### 🧘‍♀️ Solitary learners - Present: Reflective tone invites personal contemplation. - Improve: Add explicit reflection questions (e.g., “What does the Agentic Web mean for your site?”). #### 🌿 Naturalistic learners - Present: Minimal; web as an ecosystem is an implicit analogy. - Improve: Use ecosystem metaphors more explicitly (gardening, biodiversity of plugins, etc.). --- ### 📊 Accessibility Assessment #### Screen reader semantics - Present: Standard WordPress blog markup likely offers good headings and landmarks. - Improve: Ensure descriptive alt text for any event photos and clarify heading hierarchy. #### Keyboard navigation - Present: Typical WordPress themes support basic keyboard navigation. - Improve: Verify no focus traps; add skip links if missing. #### Contrast and readability - Present: Depends on theme; many Automattic‑adjacent themes meet 4.5:1. - Improve: Check contrast, line height, and font size; avoid light gray on white. #### Text resizing and reflow - Present: Responsive design likely; works at 200% zoom. - Improve: Test on mobile and desktop with zoom; ensure no clipped content. #### Media and captions - Present: Mostly text; photos (event shots) may lack detailed descriptions. - Improve: Add captions and alt text; if embedding talks, include transcripts. #### Forms and interactions - Present: None central in this post (beyond typical comment forms). - Improve: Ensure comment forms have labels, clear errors, and accessible hit targets. #### Standards reference - Map checks against WCAG 2.2 AA: 1.4.x for contrast, 2.4.x for navigation, 1.1.1 for alt text, etc. --- ### 🌍 DEIB Assessment #### Cultural breadth - Present: References global WordPress community (WCAsia, WCUS). - Improve: Add explicit recognition of contributors from various regions and languages. #### Inclusive language - Present: Generally neutral and inclusive, no exclusionary phrasing. - Improve: Reduce jargon or pair it with plain‑language explanations. #### Neurodiversity support - Present: Structured narrative with paragraphs and headings. - Improve: More sub‑headings, bullet lists, and summaries can improve scanning. #### Representation - Present: Mentions diverse roles (leadership, mentors, contributors), but not specific identities. - Improve: Include examples/stories highlighting different contributor backgrounds. #### Psychological safety - Present: Appreciative tone; “gardening” metaphor suggests shared, ongoing stewardship. - Improve: Link to community guidelines and named escalation paths for issues in AI governance. --- ### ✅ Logical Validity #### Strong reasoning - The claim that “code is effectively free” and thus brand/legacy/taste/distribution matter more is an inductive argument grounded in current AI/codegen trends; it’s coherent and matches industry experience. - The causal link between Core AI work and WordPress’s ability to remain a foundation for the open web is plausible: modern tooling is needed to keep WordPress competitive and relevant. #### Fallacies - No obvious formal fallacies. Some claims (e.g., Automattic having “all four” qualities) are value judgments but not logically inconsistent; could be strengthened with examples or data. #### Tone of voice - Tone is reflective, grateful, and optimistic, with phrases like “privilege to get to work with each day” and “we have something special, and important.” - Also mildly promotional regarding Automattic and WordPress, but balanced with genuine appreciation and acknowledgment of change. --- ### 🛡️ DARVO Analysis - Deny: The author does not deny or minimize any harms; no controversies are addressed. - Attack: No attacks on critics or opposing views; no undermining of others’ credibility. - Reverse victim/offender: The piece is not framed around victimhood; it’s a straightforward transition announcement and vision statement. - Overall: No DARVO patterns present; rhetoric is constructive and forward‑looking. --- ## 🎯 Conclusion The article marks a significant leadership transition in Automattic and WordPress Core AI, recapping rapid AI progress while reaffirming a commitment to the Open and Agentic Web with WordPress at its core. For readers, the practical next steps are to track Core AI’s evolving governance, align their own AI work with open‑web values, and watch for the author’s forthcoming AI research venture that may intersect with the WordPress ecosystem. --- ## 🧱 Refactor Appendix (append after 🎯 Conclusion) ### 📚 Literature Split Pad - Purpose: Stage Konik CEE units that become per-source Literature notes. - Split level: **H3**. - Include verbatim quotes under 25 words and a [view highlight] link. ### [H1] Automattic’s Core AI rapidly scales impact > [!quote] [Closing a chapter at Automattic](https://j.cv/closing-a-chapter/) by [an unnamed author] via [[j.cv]]. Published 2026-05-18. Accessed 2026-05-19. > “We formed Core AI, then built the AI Building Blocks, the last of which ships in WordPress 7.0.” Two lines: Core AI moved quickly from formation to shipping major features in core; shows fast‑cycle AI integration in a large OSS project. [view highlight](https://j.cv/closing-a-chapter/#H1) #xref #articleseed ID:rw_[MISSING] ### [H2] Brand and distribution outweigh code in AI era > [!quote] [Closing a chapter at Automattic](https://j.cv/closing-a-chapter/) > “(good) brand, legacy, taste and distribution matter more in an era when code is effectively free” Two lines: Argues that distribution and trust become primary moats when AI commoditizes coding. [view highlight](https://j.cv/closing-a-chapter/#H2) #xref ID:rw_[MISSING] --- ### 🔖 Atomic Split Pad (Zettel Candidates) - Purpose: Promote reusable claims into Atomic notes. - Split level: **H4**. - Each item: one idea, present tense, specific, testable. #### [Z1] WordPress remains foundation of open agentic web - Under conditions of rapid AI change, WordPress aims to stay core infrastructure for an open, decentralized, agent‑driven web. - Links: [[Open-Web]] [[Agentic-Web]] [[WordPress-Core-AI]] #### [Z2] Brand and distribution dominate when code is free - In a world of ubiquitous code generation, sustainable advantage comes from brand, legacy, taste, and distribution. - Links: [[Moats-in-AI-Era]] [[Product-Strategy]] --- ### ✏️ Fleeting Queue (Extract by Selection) - Purpose: Capture quick actions or sparks for Fleeting notes. - Extraction: **Select one line** → “Refactor: Extract selection to new note (content only).” - Keep each line short and self-contained. - [F1] Map “Agentic Web” concept to concrete WordPress use cases — context/https://j.cv/closing-a-chapter/ #fleeting #inbox - [F2] Draft meetup talk on Core AI’s evolution and governance post‑transition — context/https://j.cv/closing-a-chapter/ #fleeting #inbox - [F3] Explore funding models for open AI infra around WordPress — context/https://j.cv/closing-a-chapter/ #fleeting #inbox --- <!-- deep-read:sections end -->