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.

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