Adeline Yaw

AI Integration Specialist (Happiness Engineer) @ Automattic

Author: Adeline

  • > grep –lessons-learned ./experience/* It’s been about nine months since I took on the AI Integration Specialist role, and I wanted to share some of the things I’ve learned along the way. These aren’t polished frameworks, they’re real observations from doing the work every day. Accuracy is trust When an…

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  • > forecast –ai-support-2026 After nearly a year of working full-time on AI in customer support at WordPress.com, I’ve been thinking a lot about where this is all heading. Not in a hype-cycle, buzzword kind of way, but based on what I’m actually seeing in our data, our conversations, and our…

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  • > cat ai-squad-overview.md One of the most common questions I get from colleagues is: “What exactly does the AI Squad do?” So I thought I’d write a proper overview of how our team works, what we focus on, and why it matters. The mission The AI Squad exists to make…

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  • > changelog –role-update In July 2025, I stepped into a new role at Automattic: AI Integration Specialist for WordPress.com. After years as a Happiness Engineer helping WordPress.com users directly, I’m now leading a team focused on making AI-powered customer support smarter and more effective. Why the shift For years, I…

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