Hi Josh - I'm the same. Building solutions to these kinds of problems is really interesting.

We've not implemented that yet, but I've spoken to another company doing similar things with around 100 agents and they've managed to implement this using Twilio's conferencing facility. It's easy to drop in and out of a conference silently, which is perfect for this.

Our support is certainly not at scale, and lots more features will become appropriate as we grow, from letting people schedule callbacks to manager eavesdropping to more sophisticated management of waiting calls.

Have you built anything like this?