Do companies actually pay for software they can't justify ahead of time? It took me months to justify the costs of a damn password manager and explaining why sending passwords over email and our XMPP was a bad idea

Presumably you had to justify why keepass wasn't good enough?

That is actually what I had to justify the first time (about 4 years ago), which was the more difficult one. We had a giant spreadsheet in Google Sheets with all of our logins and everyone seemed okay with it. Convincing them it was insecure and needed to be moved to Keepass was a nightmare. This took a good half year to do.

The second time (about 3 years ago), I had to convince them that team management and selective sharing were necessary and that we should upgrade to a paid software. This took several months to get approval on, even though it's only like $400 a year for us; thankfully management seems to agree that it is worth the costs now.

To be fair, I don't consider myself very persuasive so it's entirely possible that I just did a really poor job of it.