> so you'll be dealing with a horde of product owners, compliance specialists, data privacy experts, who might never touch your product but come with excel sheets with 300 rows of gnarly questions

There is nothing like being on a call when the product isn't working right and the customer has 28 people from their side and only 2 of them know anything about the subject, but 26 of them have very strong conflicting opinions.

> If you do want to sell, treat the enterprise like an ecosystem of SMEs, find a department or team who are more innovative and sell to them behind the backs of enterprise IT. Once you've entrenched yourself and the users love you, then you can expand to other teams and eventually enterprise IT will be forced to negotiate with you for a license and do the compliance dance. But even so this will take years of effort and luck.

This is the way.

There are back-doors as well. If you can get your software on a pre-approved vendor list in a big consultancy you can by-pass a lot of the song and dance with IT. Companies like Xerox have lists like this. They sign long-term contracts with enterprise customers whose business units can use their part of the budget to get any of the software on the list.

All you have to do from there is market to the right people running those business units.

Selling through the normal IT channels is much harder. It can take 6-9 months of back and forth and you'll still likely get denied more often than not. Enterprises would rather contract with a vendor like SAP, Xerox, Microsoft, etc which is all integrated with their systems already and has the advantage of the Lindy effect in place.

the other side of this is instructive too. we've sold into mid-market accounts and the decision isn't usually 'is this better' but 'what happens to me if this breaks'. the incumbent's main feature isn't functionality, it's someone else's neck on the line if it goes wrong. the winning move for a small SaaS is afaik to get a champion inside who's willing to own that risk personally, and make sure they look very good when it works.

I agree, the risk at the CTO/CIO level is it's four years later, the startup went under, and you have this software integrated into your environment. If you're lucky, someone else will have bought it. They'll on-ramp you to their stack. But then you run the risk of their seeing your as trapped. It's not about how much money you want to pay for the product. It's about extortion.

Or, if you're less lucky, you'll left with software you can't maintain. Even if there's a contract clause that says you get all the yummy, yummy source code. You may not even be able to open source it because you don't own the copyright to some or all of the code. You just have the source code. Good luck with that.

No one gets fired for buying IBM because you know (or at least we once knew) IBM would definitely be around for years to come to support the product. Is it expensive? Yes. Have I found a lot of enterprise products miserable to use? Yes. Does everything have the stink of "well we made it work well enough not to get fired?" Yes. But you won't be getting extorted Broadcom style, or sitting around with 5,000,000 lines of AI generated source that has all sorts of hacks and work around for the four other companies to whom the startup sold their software.