Bottom-up really requires the “and up” part:

- each pricing plan targets an org scale

- and the features address those problems

That’s why websites tend to go from selling you on individual features (5 servers a month!) to team features (10 headcount!) to organization features (auto-invoice! SAML!). Your entry point is the bottom user (5 server home IOT), who convinces a manager (our team needs this!), who convinces a director (we can solve this org issue!).

The problem you’re describing is “bottom only”: if you only solve the basic problem, you’ll only attract bottom clients.

(I agree with your point about middle-out; just emphasizing the “up” part of bottom-up.)