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How a Remote Company Builds AI Fluency — Em Shreve, Automattic Transcript, AI Summary & Key Points

AI Engineer · 19 hours ago · Science & Technology · 15:33 · EN

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Automattic builds AI fluency in its remote company through two-week, in-person enablement programs that give people real time to learn — half workshops, half real project work — and by turning every graduate into a multiplier who spreads knowledge across the distributed workforce.

AI Summary

Automattic — the fully distributed company behind WordPress.com and Tumblr with over 1,400 people in 82 countries — builds AI fluency by giving employees real, dedicated time to learn rather than just handing them tools. Em Shreve, Head of AI Enablement, describes two-week in-person programs that are 50% facilitated workshops and 50% real project work, run for engineers, cross-functional teams and non-technical groups like finance and executive leadership. The engineering curriculum moves from skills, MCPs, spec-driven development and responsible AI use through building MCPs, hook systems, and autonomous agents, and is rewritten constantly as AI changes. Every graduate is turned into a multiplier through a guides program, local AI meetups, AI ride-alongs, a shared skills and MCP infrastructure (including an internal MCP server called Context Automatic), and an always-on help Slack channel. Seven cohorts of about 45 people have run so far, targeting about 600 people — roughly two-thirds of engineers — by year end. Measurement tracks intentionality, flow and sharing, with surveys at 72 hours, 30 days and 90 days showing continued growth. Projects built in two weeks include an agentic WooCommerce analytics system, a Zendesk connector, a cross-tool agent skills directory, and a guided admin support tool built by a support teammate, not an engineer.

Key Points

  • Automattic's core bet: handing people AI tools does not produce good learning or work — people need real time to learn and experiment.
  • The programs are two-week in-person immersives, 50% facilitated learning by the learning and development and AI enablement teams, 50% real project work, with peer workflow sharing and end-of-day project demos.
  • Three flavors of program: in-depth engineering cohorts, cross-functional programs combining product, engineering and design, and non-technical workshops for finance, the executive leadership team and other functions.
  • The engineering curriculum starts with skills creation, MCPs, spec-driven development and responsible AI use, then moves to building MCPs, the hook systems of Codex and Claude for extending the harness, autonomous agents running background routines, and applied WordPress AI including building a personal assistant.
  • The curriculum cannot be written once: AI changes day to day and the top model may differ with each release, so content is constantly updated to avoid teaching six-months-out-of-date material.
  • An internal MCP server called Context Automatic lets Automattic rapidly add new tooling sets and build its own governance and observability layers on top.
  • Seven cohorts of about 45 people have run so far this year, with a goal of around 600 people — about two-thirds of engineers plus other functions — through the programs by the end of the year.
  • Graduates become multipliers through a guides (champions) program of top practitioners, local AI get-togethers — about 10 run so far across world regions — AI ride-alongs showing how peers in similar roles use tools, a shared skills and MCP infrastructure, and an always-on help Slack channel where graduates answer questions.

AI in practice

Used for

Agents

  • WooCommerce agentic analytics system — Answer questions about a WooCommerce store and return answers. 2 held

Business ideas

Run immersive two-week programs, half facilitated workshops and half real project work, that take engineers, cross-functional teams and non-technical groups from AI foundations to building their own skills, MCPs and autonomous agents — then turn every graduate into an internal multiplier who teaches others.

For
Distributed companies of 1,000+ employees who have bought AI tools but see no change in how people actually work; engineering, finance, leadership and support teams.
Solves
Handing people AI tools does not change how they work. People need dedicated, protected time to learn and experiment, plus an environment where learning is the centerpiece.
  • An agentic analytics system for WooCommerce stores, letting store owners ask questions and get answers back, built during a two-week cohort
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Tools & resources

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AI Engineer is an AI engineering events and community organization operated by Software 3.0 INC. It runs flagship and regional events alongside year-round community engagement, knowledge exchange, and collaborative activities focused on practical AI engineering. Its public program includes conferences, workshops, talks, guides, and other opportunities for the global AI engineering community.

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Automattic

automattic.com

Automattic is a distributed technology company that develops and hosts web and publishing products including WordPress.com, Tumblr, WooCommerce, Jetpack, WordPress VIP, Pocket Casts, Akismet, and Gravatar. It also sponsors and contributes to open-source projects such as WordPress.org, BuddyPress, and bbPress. The company runs an internal AI enablement program using two-week, in-person cohorts that combine workshops with real project work; the program covers skills, MCPs, hooks, and autonomous agents and includes an internal MCP server, shared guides, local meetups, AI ride-alongs, and an always-on help channel.

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TypeScript
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Context

In the AINotes directory

Context is Automattic's internal MCP server for rapidly adding tooling sets with governance and observability layers. It is used in the company's AI-enablement programs, which cover MCPs, shared skills, hooks, and autonomous agents.

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OpenCode is an open-source AI coding agent developed by anomalyco. It is used as a terminal-based coding agent and external coding harness, with a beta desktop application also available. The CLI includes a full-access build agent for development work and a read-only plan agent for code analysis and exploration; the plan agent denies file edits by default and asks permission before running shell commands. OpenCode also provides a general subagent for complex searches and multistep tasks, and can be installed through its shell installer, package managers, or platform-specific desktop packages.

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WooCommerce

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WooCommerce is an open-source ecommerce platform for WordPress that lets merchants build and manage online and offline stores. It gives store owners control over checkout, data, and costs, while allowing them to choose payment methods, features, and hosting. Merchants and developers can customize stores with extensions and themes and sell locally or globally.

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zendesk.com

Zendesk is a customer service software company that provides a cloud-based service platform for support, ticketing, and customer engagement. The platform includes tools for help desks, knowledge bases, omnichannel messaging, and AI-powered automation. It is operated by Zendesk, Inc.

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Transcript

Searchable transcript of How a Remote Company Builds AI Fluency — Em Shreve, Automattic — AI Engineer (15:33). Search for a phrase, then click its timestamp to jump straight to that moment in the video.

Captions sourced from the original video on YouTube, published by AI Engineer. The video, its captions and all related intellectual property remain the property of their respective owners; AINotes claims no ownership. Provided for research, accessibility and search — see the Transcript Notice and Copyright Policy.

00:00 All >> [music] >> right. Hi everybody. Can you hear me? All right. So, uh, my name is M. Shrieve and I work at Automatic. Um, and if you're not aware of what Automatic is, we are the company behind WordPress.com and Tumblr and a number of other properties. Um, and we're a fully distributed company uh with over 1,400 uh people in 82 countries. Um, and I'm here today to talk about our approach to uh, AI enablement and upskilling our organization um, to use all of these uh, new tools and ways of working.

00:55 Um, so our bet is that you don't just get good quality learning or work out of just handing people the tools. you need to give them real time to learn and uh experiment. Um so what we've been doing is running these two week um enablement programs where we bring people in in person for a twoe immersive experience. And uh the way that we do that is um through 50% facilitated learning um through our uh learning and development team and our AI enablement team.

01:39 We pull together workshop hosts from within the company to run workshops and hands-on um activities. Uh and we'll look a bit at what that curriculum looks like shortly. Um and then 50% real project work. So, we have folks bring in um real work that they want to get done or a tool or dashboard that would help them and their day-to-day work. Um or these can also be creating new skills or MCPs to enable them to work faster outside of the program.

02:16 And another large part of this is uh encouraging peer sharing. um so sharing their own workflows to show um kind of the art of what's possible. And uh as they work throughout the two weeks, we also do a number of uh project demos at the end of each day. So we've uh we've ran three flavors of this. um our main set being for engineers where we go uh a lot more in depth um getting into applied AI.

02:51 We've also um experimented with crossf functional programs um with product engineering and design getting together in a room and discussing kind of the future of of how we all work together um with with these new tools. And then we've also extended into non-technical teams and run workshops with our finance group, our executive leadership team um and other functions as well.

03:25 So our engineering curriculum starts the first few days uh covering the basics skills and how to create them. um learning how to use MCPS and specdriven development um as well as kind of the foundations of how to use AI responsibly and how to um apply it in a way that's mindful. Um and then we start getting into deeper topics. Uh creating MCPs um for new functionality, getting into the hook system of codecs and claude and being able to extend the harness that way.

04:04 Um up to uh autonomous agents and running routines and such in the background. Um and then we end on some different applied topics. Um so again automatic is behind WordPress.com. So uh we normally run a workshop on applied WordPress AI um and some of the cool features that are in WordPress core uh around AI as well as uh being able to create your own personal assistant.

04:34 So we really try to walk people um from the foundations up into uh the ability to start creating these new things for themselves. And one thing that we found out is you cannot just write this curriculum once. As we're all aware, AI is constantly changing from day to day, week to week. The top model might be different uh depending on the latest release.

05:01 Um so we're constantly needing to update the curriculum and stay current to make sure when we running these programs, we're teaching the right thing and we're not teaching six months out of date. Um, another interesting part I wanted to highlight here is we have our own uh internal uh MCP server called context automatic. And this allows us um to rapidly add new tooling sets for MCPs that might not exist or that we want to build our own um like governance and observability layers on.

05:40 Um, and one of the cool things that, uh, I'll highlight shortly is, uh, some of the projects coming out of these cohorts is extending these abilities. So, as people go through the capabilities, um, compound and we're able to do more as a company uh, because of that. Another main focus of our program is that these aren't just a number of people that we're sending through.

06:13 We're also wanting each person we send through um to be a multiplier uh within the company and extend our reach to the folks that we can't get to yet. Um, so so far this year we've ran seven of these cohorts of groups of about 45 people. Um, and we're aiming to get around 600 people through these programs by the end of the year. Um, which is about 2/3 of our engineers as well as uh some of those other focus areas that I highlighted at the beginning.

06:53 And we would like to equip all these people with uh ways of sharing their knowledge out and again extending our reach. So we've tackled this in a few different ways. Um we are beginning a guides program or um I think other companies call this like their champions program. And what we want to do is extend our team's reach into other areas and have these um like top practitioners that we've identified within the company be able to help us out and uh continue spreading the knowledge.

07:33 Um because we're distributed, we also have began these local AI gettogethers. So people that have gone through the program um are able to then run these like little events within their regions and um run workshops and we'll help support that as well. Um and we've done about 10 of those so far in various different areas of the world. Um and it's been been exciting to see like what some of these people that have gone through the program have have gone on to do and teach.

08:08 Uh we also um organize these things called AI ride alongs and these are little workshops that we run um basically showing how you work, how you use a different tool. Um because what we found is seeing someone in your similar role or um in in a similar job to you, being able to see how they use it uh is a lot more um easy to grasp than just you know talking about the concepts.

08:40 Um and then we're also attempting to build a shared skill and MCP infrastructure. So again that context aid C um system that I mentioned but also uh encouraging people to create and share skills and build uh on top of each other's work so that we're all kind of building um towards the same kind of platform. And then we have an always on uh help Slack channel where we also ask people that have gone through this program to help out um and just kind of be available for anyone newer uh to working this way to have a place

09:22 to come and ask questions at any point of the day. So, I'm going to share a few of the the metrics that we've been tracking and um improvement we've seen throughout the program. Um, one of these is intentionality and um just applying to applying AI to your work in a more thoughtful way. Maybe these people came in at the beginning just using it as a chatbot or um you know not fully using an agentic workflow.

10:00 Um so having people be a bit more intentional at how and when they apply AI. Um flow which is like how well they're able to integrate AI into their workflows. um if people feel as if um they're able to use it in a way that makes sense for them and not just using it for AI's sake. Um and then the the sharing part again is very important to us so that we can continue um reaching other people in the company and um kind of making everyone uh a a teacher and an expert on these topics.

10:42 Um we also track uh individual lift on various metrics such as um skills and custom commands um how comfortable they feel using and applying MCPS and uh other topics like context management um and what we've seen uh from doing various surveys uh after the program. So we'll do one 72 hours after uh 30 days after and 90 days after. People will continue growing within those 90 days and um being able to apply things more and like they've had more time to experiment and try things.

11:28 Um so we're still seeing people like gain confidence and experience uh even once they've gone through the program. Um so I wanted to highlight just a few of the things that folks have built um just within the two weeks of the program. Um one of these is uh an agentic analytics system. So uh we have WordPress has a uh e-commerce platform plugin called Woo Commerce and some of the people that went through our program um created a a gentic system for asking questions about your store and getting back answers.

12:17 Um a number of folks that go through uh build on top of context a C. Um so one of our earlier cohorts [snorts] um they wanted to be able to use uh some of these tools for support um and built a Zenesk connector um which now we've had adopted through various teams throughout the company. Um we've built other providers in there that uh might not have a native MCP or again because we wanted to add additional observability there.

12:51 Um we've been building out our own agent skills directory. Uh we don't prescribe a single tool so folks are able to use codecs or claude or uh any other number of tools open code etc. Um so we wanted to build our skills directory in a way that can be used across all of those. Um and the whole skills directory actually came out out as a project from one of these cohorts as well.

13:18 Um and then finally another one I wanted to highlight here is uh guided admin support. So, um, during a help session, say you want to show someone exactly where something is, uh, within the dashboard, um, they built a tool using, uh, cloud code that allowed them to be able to, um, guide and lead a session, highlight different parts of the screen. Um, and this actually came not from an engineer, but one of our support folks um that felt a bit more comfortable after going through one of our programs.

14:01 And that is the end of my presentation. But the one takeaway that I wanted people to take from this is uh give people real time to actually experiment and learn. um you can't just throw a bunch of tools at them and expect their way of working to change. You need to to make space and give an environment for learning um and and make that like the star of whatever your education program is.

14:34 And uh I will be available for questions at our booth which is uh the automatic booth right over on the other side near that stage and the swag pickup. Um, so I'll be there for a little bit after this talk if you want to talk about anything I talked about here. Um, or you'd like to hear more about how uh how WordPress.com and Woo Commerce are uh embracing AI um with our official connections and MCPs. Um, so please stop by the booth. Um, and yeah, thank you. [applause] >> [music]