> A strategy could have been "start with a $700 offering at the top of the market and work down," but that's not something they tell you on the way in

This is absolutely the kind of thing you should be asking about and they should be telling you on the way in. As an early stage startup employee you are basically an investor. You should deeply understand how the businesses you are joining are going to work, and if they wont tell you you should consider it a red flag.