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

Handing people AI tools doesn't change how they work. Giving them real time to learn does. Em Shreve, head of AI enablement at Automattic, the company behind WordPress.com and Tumblr with over 1,400 people in 82 countries, explains how a fully remote company builds AI fluency. Their bet: people need real time to learn, not just tools. So they run two-week, in-person programs that are half workshops and half real project work, for engineers, cross-functional teams and non-technical groups like finance and leadership. She covers the curriculum (skills, MCPs, hooks, autonomous agents) and why it has to change constantly, their internal MCP server, and how every graduate becomes a multiplier through guides, local meetups, AI ride-alongs and an always-on help channel. She shares what they measure, and projects people built in two weeks, including a tool built by a support teammate rather than an engineer. In this talk: • Why AI enablement needs dedicated time, not just tool access • A two-week program: half workshops, half real project work • Turning every graduate into a multiplier across a remote company • What to measure, and what people built in two weeks SPEAKER Em Shreve, Head of AI Enablement, Automattic Website: https://emdash.codes GitHub: https://github.com/emdashcodes LINKS Automattic: https://automattic.com Automattic on X: https://x.com/automattic CHAPTERS 0:00 Intro 0:55 Our bet: real time to learn 1:15 Two-week in-person programs 1:30 Half workshops, half real projects 2:40 Engineers, cross-functional and non-technical 3:25 The engineering curriculum 4:49 Keeping the curriculum current 5:24 An internal MCP server 6:19 Every graduate is a multiplier 6:29 7 cohorts and counting 7:09 Guides and local meetups 8:09 AI ride-alongs 8:44 Shared skills and MCPs 9:04 An always-on help channel 9:29 What we measure 11:09 Surveys at 72 hours, 30 and 90 days 11:44 What people built in two weeks 12:29 A Zendesk connector 12:49 A shared skills directory 13:24 Built by a support teammate 14:09 The takeaway Recorded at the AI Engineer World's Fair 2026 in San Francisco. Subscribe for more talks from the engineers building with AI. AI Engineer: https://ai.engineer YouTube: https://www.youtube.com/@aiDotEngineer X: https://x.com/aiDotEngineer LinkedIn: https://www.linkedin.com/company/aidotengineer/ #AIEnablement #AIAdoption #AIEngineer