People constantly moan about their jobs, stupid processes, broken software and tools... listen to them and build something better.
The problem is that usually the moaners are not the loaners - they're not the ones making the purchase decisions.
That's why you either get in via very small business (where the owner is the buyer and user) or guerrilla (like Slack et al).
The people moaning are the ones building things that can be built better, not the ones that you should try to sell to.
I'm a moaner, but I'm not building anything.
The software my school uses to communicate with parents is fucking awful. Based on digging around their website & linkedin, I suspect they have a team of offshore developers - which is fine - but my money is that they don't actually have a team, they're paying a company that gives them supposedly-fungible engineer-hours instead of an actual cohesive team that works on the product and is proud of what they've made. They just eat requirements and shit something approximating software.
But what am I going to do? Say I build a competitor, solo, for cheap. (It can be done. The software doesn't do much. The hardest thing would be ensuring the emails actually get delivered.)
Now I get to play salesman. I have to sell it to my school. Now I have to maintain it. Our school isn't rich; a local school paid $130k for an unrelated hardware+software solution, so I'm at most going to get that, and now I'm on call 24/7, now I'm training the teachers & administrators to use it, now I'm fielding support emails, etc., etc.
Fuck it. I'll keep moaning.
This is a perfect example. The school is suffering, but has nearly no budget. The users suffer, but have no say. Nothing changes, everyone cripples along.
Is this true? I've tried for months to get people to talk to me about their problems and the most common answer I get is "everything's... fine?".