Toby
Toby is betting that the scariest part of job hunting is the moment you sit across from someone who gets to decide your future. Practicing on friends has a ceiling. They know you, they're nice, and they don't ask the weird behavioral questions that actually trip people up. An AI hiring manager removes the niceness and the familiarity, which might be exactly what anxious candidates need.
I'd want to know how deep the realism goes. Does Toby just ask questions, or does it push back, follow up, and react to your answers the way a real interviewer would? Does it know the difference between a product manager interview and a data science one? The value lives in the follow-up questions, not the initial script.
The bigger picture is that interview practice has been shockingly underserved. People pay coaches hundreds of dollars for a few sessions, or they wing it. If Toby can get the simulation good enough, it could become the default way people prepare. I'm interested to see how it handles feedback and whether it tells you where you actually screwed up, because that's where the real learning happens.