Reflections, Progress, and Where We Go Next  > [!note]+ Document Notes > --- > tags: [WordPress, Automattic, product-strategy] > author: Pedraum Pardehpoosh > source: LinkedIn > reference: [https://www.linkedin.com/pulse/reflections-progress-where-we-go-next-pedraum-pardehpoosh-zrs1f/] > date created: 2026-01-19 00:00 > --- > # 🏷️ Title: Reflections, progress, and where we go next > ## 🧭 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: Automattic’s Product Development Council set a 3–5 year product vision, executed a “Year of Product Quality,” and reflects on progress in quality, hosting, AI site building, and organizational foundations. > - Why it matters: It clarifies how Automattic will build high-quality products at scale, with stronger product discipline and customer empathy. > - Key stakeholders: Product, Engineering, Design, Operations leadership, CEO, and teams working on WordPress.com, Woo, hosting, and AI tools. > - Risks and tradeoffs: Tension from functional reorgs, the “messy middle” of culture change, and the need to deepen existing work instead of chasing new projects. > - Bottom line: The vision stands; 2026+ is about methodically strengthening foundations—quality, product rigor, hosting, commerce, AI, and developer experience. > ## 📖 Main Content > - The council met a year ago in Automattic’s NoHo office to align on a 3–5 year vision and “lines of action” (Fit & Finish, Onboarding, Migrations, Retention), framing 2025 as the “Year of Product Quality” ([opening context](https://read.readwise.io/read/01kf9ferwrmm8ewycef9zjbp03?endLexposition=0000C_00000-006L&startLexposition=00002&emphasizeText=3%E2%80%935-year+horizon+and+a+set+of+clear+lines+of+action+for+the+year+ahead)). > - Fit & Finish: a quality sprint led by Design and Engineering closed 293 bugs and created a new quality operating model, plus accessibility work for Woo and an Algolia-powered marketplace search to improve discoverability ([quality section](https://read.readwise.io/read/01kf9ferwrmm8ewycef9zjbp03?endLexposition=0000I_00000-005l&startLexposition=0000E&emphasizeText=2025+was+the+Year+of+Product+Quality)). > - Migrations: direct engagement with Woo merchants migrating to Pressable and WordPress.com, plus a self-serve Shopify migration guide and 17+ fixes to the Substack Importer to reduce import errors and boost successful migrations ([migrations focus](https://read.readwise.io/read/01kf9ferwrmm8ewycef9zjbp03?endLexposition=0000Q_00004-0001&startLexposition=0000O&emphasizeText=self-serve+Shopify+migration+guide+as+part+of+the+new+user+experience)). > - Retention: allowing plugins on all plans reduced refunds by solving a key churn driver; a cross-functional effort helped large Woo merchants with scaling pain, and Freshly Pressed returned as an AI-powered curated showcase to drive author engagement ([retention work](https://read.readwise.io/read/01kf9ferwrmm8ewycef9zjbp03?endLexposition=0000U_00000-0091&startLexposition=0000S&emphasizeText=Allowing+plugins+on+all+plans+has+led+to+a+decrease+in+average+refund+rates)). > - Hosting & developers: new designs for Site List, Site Overview, and Site Settings plus a multi-site dashboard opt-in aim to simplify site management; Studio evolved into a credible local-to-cloud workflow via Studio Sync, WordPress Studio, Blueprints, CLI improvements, and deeper integration with WordPress.com and Pressable ([hosting and Studio](https://read.readwise.io/read/01kf9ferwrmm8ewycef9zjbp03?endLexposition=0000a_00002-003A&startLexposition=0000Y&emphasizeText=shipped+a+new+design+for+Site+List%2C+Site+Overview%2C+and+Site+Settings)). > - AI site building: the WordPress.com AI Website Builder launched in April 2025 and now powers 15%+ of all new sites, validating AI as a faster on-ramp for non-technical creators; the Creators group improved lightweight publishing, Gutenberg mobile editing, Fediverse connections, and reintroduced Freshly Pressed to grow audiences ([AI builder impact](https://read.readwise.io/read/01kf9ferwrmm8ewycef9zjbp03?endLexposition=0000e_00004-006v&startLexposition=0000c&emphasizeText=has+scaled+to+power+15%25%2B+of+all+new+WordPress.com+sites)). > - Structural foundations: Automattic’s functional org model matured; Product–Engineering–Design trios became the norm; Product Ops set up planning/review rituals; Linear became the single source of truth; Jobs To Be Done (JTBD) and the Product Compass help align on customer value and CEO priorities ([foundations list](https://read.readwise.io/read/01kf9ferwrmm8ewycef9zjbp03?endLexposition=0000k_0000B_00000-0021&startLexposition=0000g&emphasizeText=Beyond+features+and+initiatives%2C+we+made+structural+progress)). > - The “messy middle”: moving to functional orgs while deepening cross-team collaboration created tension, which the author frames as natural and even productive (“guitar music is produced through the tension of the strings”) ([messy middle metaphor](https://read.readwise.io/read/01kf9ferwrmm8ewycef9zjbp03?endLexposition=0000s_00000-003f&startLexposition=0000q&emphasizeText=Moving+to+a+functional+organization%2C+while+asking+teams+to+collaborate+more+deeply)). > - Product discipline: a major learning is the need for more disciplined concept development—ideas → concepts → PRDs—with deeper customer understanding, better problem framing, strong concept briefs, and PRDs that define “What” not “How” ([concept pipeline](https://read.readwise.io/read/01kf9ferwrmm8ewycef9zjbp03?endLexposition=00016_00000-002g&startLexposition=0000y&emphasizeText=We+learned+that+we+need+discipline+in+how+ideas+become+concepts)). > - Customer empathy: JTBD work, weekly walkthroughs, and end-to-end flow reviews uncover subtle quality gaps that a roadmap-only process would miss ([customer empathy as renewable](https://read.readwise.io/read/01kf9ferwrmm8ewycef9zjbp03?endLexposition=0001A_00000-003e&startLexposition=00018&emphasizeText=customer+empathy+is+a+renewable+resource+if+we+invest+in+it)). > - Philosophy of quality: “Quality, at every layer of the stack: product, process, and craft” is asserted as the core culture; the PDC concludes they need deeper work on existing projects, better-formed concepts, consistent experience reviews, and clear PED accountability ([quality as culture](https://read.readwise.io/read/01kf9ferwrmm8ewycef9zjbp03?endLexposition=0001Q_00000-001G&startLexposition=0001G&emphasizeText=Quality+is+not+an+initiative%3B+it%E2%80%99s+the+work)). > - 3-year horizon: the original vision stands; 2026+ is about sharpening Product’s “Why,” empowering Artistic Directors and Product Owners on “What,” and supporting Engineering and Design on “How and When,” with processes that match ambition and deliver material quality improvements ([3-year horizon reset](https://read.readwise.io/read/01kf9ferwrmm8ewycef9zjbp03?endLexposition=0001c_00000-001t&startLexposition=0001S&emphasizeText=Re-establishing+the+3-Year+Horizon)). > - Closing tone: the author expresses gratitude and resolve, reconnects the work to Automattic’s mission of democratizing publishing, commerce, and messaging, and calls for “marching along this mystical path using practical feet, with quality at the center” ([closing reflection](https://read.readwise.io/read/01kf9ferwrmm8ewycef9zjbp03?endLexposition=0001u_00000-002G&startLexposition=0001e&emphasizeText=Let%E2%80%99s+keep+marching+along+this+mystical+path)). > ### 🗒️ Notes > - The piece opens with a PDC offsite a year ago, which set a 3–5 year horizon and “lines of action” (Fit & Finish, Onboarding, Migrations, Retention) as a way to improve product culture and  ##### Pedraum Pardehpoosh One year ago, in the cold of January, the [Automattic](https://www.linkedin.com/company/automattic?trk=article-ssr-frontend-pulse_little-mention) Product Development Council (leadership from Product, Engineering, Design, Operations, and our CEO) gathered in the NoHo office to craft a long-term product vision for Automattic. We left that week aligned on a 3–5-year horizon and a set of clear lines of action for the year ahead. At the time, it felt like the beginning of a new chapter, with clarity, collaboration, and renewed commitment to craft at its core. Twelve months later, that chapter is still being written. We’ve made meaningful progress. We’ve learned (through doing) where our operating model supports great work, and where it falls short. And we’re entering this new year with something even more important: a shared understanding of what it means to build high-quality products at scale. I write this post with humility. What follows is not just a recap, it’s a re-commitment. I know we’re not where we want to be, but we’re in the midst of massive changes, including cultural shifts. This is no small feat. ##### What We Achieved This Year When we established our lines of action (Fit & Finish, Onboarding, Migrations, and Retention), we expected them to become the foundation for a stronger product culture, and they did. But the real story of the year is the thousands of individual decisions and improvements made by teams across the company. The work ahead of us along these lines of action remains, but it’s nice to take a beat. ##### Fit & Finish / Quality 2025 was the Year of Product Quality. A refocused quality sprint, led by Design and Engineering, closed 293 bugs in the first half of the year and established a new quality operating model, setting a higher and more sustainable quality bar. We completed the Woo Core Frontend Accessibility Audit and refreshed our Accessibility Hub work, raising the baseline quality and compliance of key merchant flows. We also upgraded Woo Marketplace categorization + search for connected stores to use Algolia, improving relevance and discoverability so merchants can find and buy what they need more reliably. ##### Onboarding We’ve been evolving WooPayments onboarding to balance time-to-first-transaction with better compliance + risk controls. WordPress Mobile also shipped a refreshed [WordPress.com](https://www.linkedin.com/redir/redirect?url=http%3A%2F%2FWordPress%2Ecom&urlhash=4EOS&trk=article-ssr-frontend-pulse_little-text-block) onboarding experience, making the path from download to first publish smoother. ##### Migrations We engaged hands-on with Woo merchants to migrate them to Pressable and [WordPress.com](https://www.linkedin.com/redir/redirect?url=http%3A%2F%2FWordPress%2Ecom&urlhash=4EOS&trk=article-ssr-frontend-pulse_little-text-block) hosting, and to ensure they have a performant, pleasant experience. We also shipped a self-serve Shopify migration guide as part of the new user experience, along with 17+ fixes to the Substack Importer. This improved paid and free subscriber imports, driving import errors to near zero and increasing successful creator migrations to [WordPress.com](https://www.linkedin.com/redir/redirect?url=http%3A%2F%2FWordPress%2Ecom&urlhash=4EOS&trk=article-ssr-frontend-pulse_little-text-block). ##### Retention Allowing plugins on all plans has led to a decrease in average refund rates, as it addressed one of the main reasons for refunds and cancellations, according to our earlier research. We ran a cross-functional effort to retain large merchants at risk of churn by addressing scaling pain, and we’re using those learnings to inform a more optimized Woo hosting offering. Freshly Pressed returned as a curated showcase of standout posts, powered by AI and surfaced across Reader, WP Admin, and mobile, driving measurable engagement improvements for these authors. ##### Cross-Initiative Progress ##### Hosting & Developers We shipped a new design for Site List, Site Overview, and Site Settings in the existing Hosting Dashboard, and shipped the remaining redesigned experience with the Multi-site Dashboard opt-in, a major milestone toward simpler site management. We also delivered a year of sustained Studio evolution, launching Studio Sync and WordPress Studio while significantly improving scale, stability, Blueprints, CLI tooling, and [WordPress.com](https://www.linkedin.com/redir/redirect?url=http%3A%2F%2FWordPress%2Ecom&urlhash=4EOS&trk=article-ssr-frontend-pulse_little-text-block) and Pressable integration to establish a credible local-to-cloud workflow. All of these are efforts towards simplification of the hosting experience, especially for customers with multiple sites. ##### Site Building with AI Since its official April 2025 launch, [WordPress.com](https://www.linkedin.com/redir/redirect?url=http%3A%2F%2FWordPress%2Ecom&urlhash=4EOS&trk=article-ssr-frontend-pulse_little-text-block)’s AI Website Builder has scaled to power 15%+ of all new [WordPress.com](https://www.linkedin.com/redir/redirect?url=http%3A%2F%2FWordPress%2Ecom&urlhash=4EOS&trk=article-ssr-frontend-pulse_little-text-block) sites — validating AI site building as a faster path for non-technical creators to get online. The Creators group also made it easier to publish, grow, and reach new audiences across the web, mobile, and the open social web. We added lightweight publishing in the Reader, relaunched Freshly Pressed, improved mobile editing with GutenbergKit, and expanded Fediverse connections to help creators grow beyond traditional channels. ##### Strengthening the Foundations Beyond features and initiatives, we made structural progress: * The functional organizational model matured, even if unevenly. * Product, Engineering, and Design (PED) Trios became the default, not just a structure, but a habit. * Product Ops established essential rituals for planning, reviews, and alignment. * Linear became a single source of truth for initiatives. * Jobs To Be Done gives us a framework for seeing through our customers’ eyes. * The Product Compass process provided a consistent mechanism for evaluating quality, prioritizing, and alignment with our CEO. ##### What We Learned I’ll be honest: this year was not a tidy progression. I didn’t expect it would be based on my experiences at other companies that made similar moves. ##### We learned what “the messy middle” really feels like. Moving to a functional organization, while asking teams to collaborate more deeply on shared initiatives, will always generate tension. We felt it. That’s ok, though. Guitar music is produced through the tension of the strings. ##### We learned that quality is fractal. It shows up in the code, in the design. And it shows up in how we define, review, and connect the work. And it importantly shows up in how we sequence and scope. ##### We learned that we need discipline in how ideas become concepts, and concepts become PRDs. This was one of the most important outcomes of the recent PDC meetup. Product must consistently produce more well-formed work than Engineering can take on. That means: * Deeper customer understanding * Better problem framing * Clearer articulation of Why * Concept briefs that pass a high bar * PRDs that define What, not How These are the things that world-class organizations do. High-performing product organizations are really good at concept refinement. We’re sharpening that muscle now. ##### We learned that customer empathy is a renewable resource if we invest in it. Our ‘Jobs to Be Done’ work, weekly walkthroughs, and end-to-end flow reviews are beginning to reveal quality gaps that would have been invisible in a traditional roadmap-only process. This is a strength we’ll continue to flex. ##### A Renewed Focus: Quality Above All If last year’s theme was Back to Basics, this year’s theme is even simpler: ##### Quality, at every layer of the stack: product, process, and craft. Quality is not an initiative; it’s the work. It’s the job. It’s the culture we’re building. The end-of-year PDC meetup reinforced this: we don’t need a longer list of new projects, we need deeper work on the ones already in motion. We need better-formed concepts before they hit Engineering. We need consistency in how we review, refine, and elevate customer experiences. And we need clarity of accountability across Product, Engineering, and Design. ##### Re-establishing the 3-Year Horizon Last January, we set a vision for the next 3–5 years. That vision still holds. The opportunities in hosting, site building, developer tools, and commerce remain enormous, and uniquely ours. But the way we get there must be methodical. This year is about strengthening the foundation: * Sharpening Product’s role in defining “Why.” * Empowering Artistic Directors and Product Owners to articulate “What.” * Supporting Engineering and Design as they determine “How and When.” * Making our processes reflect our ambition * Driving material improvements in quality across the experience If we do this well (and I believe we will), the next phase of our vision becomes not only achievable, but inevitable. #### Looking Ahead As I reflect on this year, I feel a combination of gratitude and resolve. Gratitude to our teams for their resilience. Gratitude for the candor and collaboration across Product, Engineering, and Design. Gratitude for the patience we’ve shown one another as we adapt to a more disciplined way of working. And resolve, because while there will be more bumps, we’re committed to building this new way of working, together. We operate in a world that feels increasingly fractured. Yet our mission remains steadfast: democratize publishing, commerce, and messaging. Not just because it’s good business, but because it makes the web a better place, and the world a little more open, a little more human, and a little more hopeful. Thank you for everything you’ve done over the past twelve months, and for everything we will build in the next. Let’s keep marching along this mystical path using practical feet, with quality at the center, craft in our hands, and makers in our hearts., Reflections, Progress, and Where We Go Next, Pedraum Pardehpoosh, 01kf9ferwrmm8ewycef9zjbp03.