Whereas you can pretty much agree to any terms that don’t misrepresent how your product works when you’re just starting out, there comes the point of wanting to spend a lot more scrutiny on your contracts without having in-house legal yet.
If you’re a founder, that probably means you will be sending redlines, thinking about indemnities and warranties and handling other wonderful aspects of doing business internationally (privacy terms, jurisdiction, insurance, …).
While true that price discrimination helps to make these cases mostly worth it, they are still a crazy time suck and finding a savvy lawyer to take it off your hands may or may not be easily possible (lawyer fees for one such deal once ended up being 50% of the whole deal value - we raised enterprise prices after that).
Watch out especially when you’re in an industry going through lots of M&A activity as your self-service customers may suddenly be part of large Fortune 500 organizations, and despite all advice to the contrary, stakeholders who know your pricing already do balk at your 5-10x Enterprise prices.
I do wish there were more stories of how the legal side of these deals is dealt with, what sticking points in contracts take up most of your time, and what „hacks“ you found.
(One hack that saved me a lot of time: Treat your terms like you would any other part of your product. Iterate, work on the UX, remove barriers to adoption. After a bunch of gnarly negotiations over things that matter to your client, but not usually to you I compiled a list of changes and had our lawyer revise the terms to avoid the need to negotiate those parts moving forward. Alas, it’s a moving target and we’re in the midst of another iteration like this.)