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Lessons from leading AI initiatives in customer support
> 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 AI bot gives a wrong…
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Where AI in customer support is heading
> 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 day-to-day work. AI is getting…
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Inside the WordPress.com AI Squad: how we improve our bots
> 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 WordPress.com’s AI support bot as…
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New chapter: AI Integration Specialist at Automattic
> 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 watched AI tools evolve from…
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