> 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 better at knowing what it doesn’t know
One of the most important developments I’ve seen is AI getting better at recognizing its own limitations. Early on, bots would confidently give wrong answers. Now, the best systems know when to say “I’m not sure about this, let me connect you with a human.” That self-awareness is a game-changer for user trust.
The human-AI handoff is the new frontier
The moment a conversation moves from bot to human support is critical. Do it too early, and you lose the efficiency benefits of AI. Do it too late, and the user is frustrated. Getting that transition smooth and seamless is one of the biggest areas of focus for teams like ours, and I expect it to be a major differentiator for support organizations in the coming years.
Quality evaluation needs to evolve
How we evaluate AI support quality today is still largely manual. Our AI squad reviews conversations, scores them against criteria, and identifies patterns. That’s valuable, but as volume scales, we’ll need smarter ways to evaluate at scale. Think automated quality scoring, anomaly detection, and real-time accuracy monitoring. The teams that figure this out first will have a serious advantage.
AI doesn’t replace empathy
No matter how good AI gets, customer support will always need a human heart. AI can handle the “what” and the “how” but the “I understand how frustrating this must be” still needs to come from a real person. The future isn’t AI vs. humans. It’s AI and humans working together, each doing what they do best.
What I’m excited about
I’m genuinely optimistic about where we’re heading at WordPress.com. The work we’re doing with our Bots, the investments in AI quality, and the cross-team collaboration across divisions and teams, it all points toward a support experience that’s faster, smarter, and more caring. And I’m proud to be part of building that future.
Leave a Reply