[wavemode]

The main cause of this phenomenon is the simple fact that, many B2B startups are going to try their hardest to charge you the maximum you can afford, rather than a standard price. So their first job is to figure out how deep your pockets are.

Another cause is that, a lot of B2B startups are building the plane while flying it - they don't actually have all of the enterprise features they claim to have (or at least, the features aren't yet generalized enough - think "if customer.name == 'BigCo' then DoBigCoThing()" type of code). So they need to figure out what your needs are, and thus what things will need to be cobbled together by the time the deal closes.

[milesvp]

It doesn’t even have to be as nefarious as trying to maximally charge. Very often what seems like a simple product offering can actually be quite nuanced with services or goods bundled or unbundled. I’ve listened to many sales calls where the buyer was asking for the wrong thing, and giving a quote for that thing doesn’t really do anyone any good. In my experience the best sales people are really trying their best to tailor their offerings to the needs of the customer even going so far as pointing them at cheaper products or even another company if it fits their needs better.