Support in hosting is usually built around speed. How fast can you resolve a ticket, close the chat, and move on. In this episode, Jesse Friedman and Sanja Grbic question that model and imagine something better. They discuss async, mobile-first communication that lets customers ask questions on their own time without feeling tied to a desk or a ticking clock.
Sanja, a senior product designer at Automattic, shares the WooCommerce merchant chat tool she helped build in six days. It lets shoppers ask questions right on the site, gives merchants a simple inbox to reply on the go, and can let AI answer straightforward questions automatically. The goal was never speed for its own sake. It was creating an experience where people feel comfortable having a real conversation.
Along the way, Jesse and Sanja talk about how AI is changing design and engineering roles, why open source lets hosting companies build their own tools, and how Automattic's habit of working in public keeps quality high. This is a thoughtful conversation about product, support, and the future of how hosting teams work.
- 500 people vibe-coded for 30 days. I was one of them. - Sanja Grbic, Automattic
- AI Engineers World's Fair
- Sketch
- Bespoke Post
- P2
Click here to watch a video of this episode.