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Meet Odie: the view from the support side
My colleague Adrián Gómez wrote a post about Odie, the AI assistant behind WordPress.com and WooCommerce support: Meet Odie. Back in August I wrote about how Odie decides when to hand a conversation to a person. Adrián covers a different part: how the support team thinks about Odie, and why putting a bot in front…
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I’m speaking at AI Engineer Sydney
I’m speaking at AI Engineer Sydney this December. My talk is called “Half our handoffs are the bot’s idea.” The talk is about part of my work on the Dotcom AI Squad at WordPress.com and how our AI support assistant decides when to hand a conversation to a person. (A handoff is when the assistant…
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Building a drum practice site with Claude and Spacefast
I play the drums, and my son has started learning too. I wanted a quick place we could both go to for rudiments. Rudiments are short practice patterns for your hands, and most drumming is built from them. My son could practise along with it, and I could brush up on paradiddles and the other…
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Deflection is not a support strategy
Job Thomas on why AI didn’t create the problem in support, it made it easier to see.
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How our support bot decides to get you a human
Most people have been stuck with a support bot that won’t let them through. I work on the opposite problem, teaching ours to notice when it should step aside.
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Lessons from leading AI initiatives in customer support
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 answer, it doesn’t just…
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Where AI in customer support is heading
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 better at knowing…
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Inside the WordPress.com AI Squad: how we improve our bots
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 accurate, helpful, and…
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New chapter: AI Integration Specialist at Automattic
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 simple chatbots into…
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