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

summarized

TLDR

Automattic's AI upskilling program is built on the claim that giving people AI tools without dedicated time to learn and experiment does not change how they work. The fully distributed company of 1,400+ people runs two-week in-person cohorts split between facilitated learning and real project work, with a goal of getting roughly 600 engineers through this year. Program participants have produced infrastructure that outlives the cohorts, including an internal MCP server and a Zendesk connector now used across multiple teams.

Key points

Automattic runs two-week in-person AI enablement cohorts split 50/50 between facilitated learning and real project work.

Seven cohorts of about 45 people have run so far, targeting 600 engineers by year end.

Automattic built an internal MCP server called context automattic with custom governance and observability layers.

A support employee, not an engineer, built a guided admin support tool using cloud code after the program.

Survey results show participants keep gaining confidence and skills 90 days after finishing the program.

Tools mentioned

Techniques

  • Two-week immersive enablement combining facilitated learning with real project work
  • Spec-driven development
  • AI ride-alongs, live workshops demonstrating how peers in similar roles use AI tools
  • Peer sharing of workflows across the company
  • Cohort multiplier model where program graduates train others through guides and local events
  • Internal MCP server as shared tooling infrastructure with custom governance and observability
Transcript (captions)

0:00 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

0:23 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

0:37 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

0:55 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

1:14 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

1:30 through 50% 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

1:45 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

2:00 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

2:16 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

2:34 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

2:51 depth um getting into applied AI. We've also um experimented with crossf functional programs um with product engineering and design getting together in a room and

3:04 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

3:18 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.

3:35 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

3:50 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

4:04 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 again automatic is behind WordPress.com. So uh

4:22 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

4:36 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

4:51 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

5:04 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.

5:17 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

5:34 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

5:50 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.

6:04 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

6:19 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

6:38 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

6:53 the beginning. 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

7:08 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

7:25 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

7:39 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

7:55 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

8:06 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

8:20 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

8:36 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

8:49 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

9:07 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

9:22 working this way to have a place 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

9:36 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

9:50 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 at how and when they

10:05 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

10:21 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

10:40 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

10:57 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

11:12 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

11:28 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 wanted to highlight just a few

11:46 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

12:05 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

12:33 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

12:47 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

13:00 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

13:16 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,

13:32 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,

13:48 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.

14:18 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

14:32 your education program is. 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

14:47 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

15:04 embracing AI um with our official connections and MCPs. Um, so please stop by the booth. Um, and yeah, thank you. [applause] >> [music]

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