Two hard calls
Exposing the AI instead of hiding it. The automation was the product, and it was also the problem. The better the AI got, the more it unsettled the people relying on it, so they policed every reply by hand and the value evaporated. The tempting move was to make the AI feel more finished and hide its work. I bet the opposite: build a QA surface where users could easily follow what the AI was doing and grade its answers. For the client, that was the control they had been missing, the reason they no longer needed to check every reply themselves. For the company, every grade was structured feedback that fed straight back to the engineers retraining the models. The same surface answered both sides at once, and control and trust stopped competing and started reinforcing each other.
Refusing the familiar-versus-different tradeoff. The founders wanted a look and feel radically unlike Zendesk, so the product would never be mistaken for one more ticketing tool. Sales wanted the opposite: the more familiar it felt, the easier it was to sell. Rather than pick a side, I went looking for a third option. It took several rounds of sketching and dead ends before the Insight card emerged as the synthesis. Instead of a flat queue of tickets, the platform grouped messages into cards by type, then let teams filter them by relevance and urgency against their own goals, so anyone could see what to handle next. It gave the human team an intelligence layer even over the messages the AI could not answer, and it read as something genuinely new rather than a reskinned help desk. Familiar enough to sell, different enough to matter.