How a Remote Company Builds AI Fluency — Em Shreve, Automattic

All right. Hi, everybody. Can you hear me? Cool. All right, so, uh, my name is Em Shreve, and I work at Automattic. Um, and if you're not aware of what Automattic 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 fourteen hundred, uh, people in eighty-two 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. 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 two-week immersive experience. And, uh, the way that we do that is, um, through fifty percent facilitated learning, um, through our, uh, learning and development team and our AI enablement team. 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 fifty percent 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 in 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. 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. We've also, um, experimented with cross-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.

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 spec-driven 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 Codex and Claude, and being able to extend the harness that way, 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 a-again, Automattic 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. 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. Um, so we're constantly needing to update the curriculum and stay current to make sure when we are 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 Automattic, 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. 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, 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. 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 forty-five people. Um,

and we're aiming to get around six hundred people through these programs by the end of the year, um, which is, uh, about two-thirds of our engineers, as well as, uh, some of those other focus areas that I highlighted at the beginning. And we would like to equip t- 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. Um, because we're distributed,

we also have began these local AI get-togethers. 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 ten 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. 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. Um, and then we're also attempting to build a shared skill and MCP infrastructure. So again, that context agency, 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 to come and ask questions at any point of the day.

So I'm gonna 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.

Um, so having people be a bit more intentional about how and when they apply AI. Um, flow, which is, like, how well they're able to integrate AI into their workflows. Um, if f- 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. 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 seventy-two hours after, uh, thirty days after, and ninety days after, people will continue growing within those ninety days and, um, being able to apply things more and, like, they've h- had more time to experiment and try things. Um, so we're still seeing people, like, gain confidence

and experience, uh, even once they've gone through the program.

Um, so I just 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 ha-- WordPress has a, uh, e-commerce platform plugin called WooCommerce. And some of the people that went through our program, um, created a

agentic system for asking questions about your store and getting back answers. Um, a number of folks that go through, uh, build on top of Context A and C. Um, so one of our earlier cohorts, um, they wanted to be able to use, uh, some of these tools for support, um, and built a Zendesk 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. 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 Codex or Claude or, uh, any other number of tools, OpenCode, et cetera. 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. Um, and then finally, another one I wanted to highlight here is, uh, guided admin support. So, um, during a help session, say you wanna 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. 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.

And, uh, I will be available for questions at our booth, which is, uh, the Automattic 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 wanna talk about anything I talked about here, um, or you'd like to hear more about how, uh, W- how WordPress.com and WooCommerce are, uh, embracing

AI, um, with our official connections and MCPs. Um, so please stop by the booth. Um, and yeah, thank you.