You should look at WordPress VIP, GitHub for Enterprise, etc. as a guideline. I would caution you against doing an on-prem installation, as you'll have to learn

You should look at WordPress VIP, GitHub for Enterprise, etc. as a guideline. I would caution you against doing an on-prem installation, as you'll have to learn the ins and outs of their organization, deal with their server setup ("Oh, you used Ubuntu? We use RHEL 5, is that a problem?") and would need to find some alternative to S3 for your backing data. And as others will no doubt point out: charge a lot more. In some cases, Enterprise pricing is more like a Veblen Good (https://en.wikipedia.org/wiki/Veblen_good https://en.wikipedia.org/wiki/Veblen_good) if you only charged say $25/month they would realize that your thing is junk, but the same thing for $250/month sounds very desirable.