Sales to governments will likely come with even more compliance requirements, national security audits, and potentially staff vetting. It’s not worth it early on unless you’re really well funded.
Compliance does actually scale with the business, so it’s not particularly onerous at the start. Although it can get out of hand if you’re not careful. Compliance should be pragmatic.
SSO is clearly one of the major factors for integrating anything into an enterprise organisation. Their IT team will want to have complete control over who has access, when somebody leaves the company they want to make sure that they can shut them down immediately, not have to reach out to third-party providers, or login to multiple systems. Ignore this at your peril.
Independent penetration tests are also really important.
You can usually resist requests for self-hosting or multi-tenancy if you have all the above, but not always. If they don’t think you’ll be around tomorrow, then they won’t touch you.
That's the position we're in, though as an older but still growing B2B we have to do this for existing customers as well.
We're in the process of getting ISO27001, meanwhile we got one guy out of 40ish almost full-time answering such questions now.
This all becomes easier if you turn it from an engineering problem to an operations problem. Enterprise really cares about how you operate in order to guarantee they won’t be negatively impacted by your system. SOC2 is much more about your operations than anything else.
My recommendation: have a multi-tenant system for the plebs and bespoke deployments for the enterprise. Save yourself the headache of trying to satisfy both with the same infrastructure.