Even a midsize company wants SSO (which is $7 a seat through Microsoft) and don’t want to have to worry about onboard and off board users individually to every SaaS product they use

Any midsize company that would trust having their proprietary information like would be in one on ones would be a complete idiot to depend on a random website.

One on ones usually feed into reviews. What guarantees would their be that the site would be up in a year?

Interesting theory.

IRL: I could add whatever I wanted into my computer at most places I've worked, including multi-billion$ international companies.

Can you put your company’s proprietary information on any website? Sure I can put anything on my work computer.

If your company wouldn’t mind you putting details of your 1 on 1s on his website, do you mind just emailing me those notes?

Yes it would be kind of crazy to do that wouldn’t it?

Enterprise shouldn't be the bar for caring where you store your data. Just putting data anywhere needs to end.

It's a proxy for amount. More data = more risk

Data tends to be valued based on volume/amount; enterprises have more data and with it comes more risk. As a result, they vet vendors more rigorously to control the risk.

Vetting vendors has a fixed cost. On the small end, it becomes challenging to bootstrap a business when you have a high amount of fixed costs so it's often forgone until a size threshold is reached. This same sentiment is frequently reflected in government regulation as well

Would you be okay with your doctor putting his notes on you in the website? Would you be okay with your accountant putting all of your financial data here?