I think the problem with your business model is:
- People who have already built their company/website/product are not going to move the world to adopt your platform. It's just too much work.
- This leaves you with people who haven't built/shipped anything yet, who aren't really willing to pay $500-2000 for your software (there may be exceptions, but not thaaaat many).
I think a really successful business model would be something like:
- Free for the first $10k revenue
- 3% of revenue after that (auto calculated via Stripe)
This way, many more people will get started with your software, and those that are actually successful will end up paying you a lot more than $500. "We don't get paid till you do" is the headline on your pricing page.
I'd imagine your retention would be amazing because it'd be very difficult to move off (similar reasons as Stripe, AWS).