> A lot of software gets a foothold in an org by starting with the ICs, and individuals, not groups, are often the ones that request or approve software.

Not really. Even if we keep the conversation in the realm of startups (which are not representative of anything other than chaos), ICs have essentially no ability to take unilateral financial risk. The Github “direct to developer” sales model worked for Github at that place and time, but even they make most of their money on custom contracts now.

You’re basically picking the (very) few services that are most likely to be acquired directly by end users. Slack is like an org-wide bike-shedding exercise, and Github is a developer tool. But once the org gets big enough, the contracts are all mediated by sales.

Outside of these few examples, SaaS software is almost universally sold to non-technical business leaders. Engineers have this weird, massive blind spot for the importance of sales, even if their own paycheck depends on it.