Is it any easier to get a job that'll pay or accommodate for a Masters, compared to for a Bachelors?

I've known of a few people who've had jobs put them through a Masters, or offered it at least. One was for psychology (third sector social services), MBA and the other I forgot (probably management-related). I did know one person in HR management who was asked to do an undergrad to progress further (they didn't take the offer as they don't like school. They eventually advanced by moving to another employer). I've not known anyone say they got a job somewhere, they did an undergrad through the employer (so not talking about applying for a publicly-listed apprenticeship job). I suppose it would make sense if Masters are funded more often, since a one year full-time Masters is cheaper and quicker than a 3-year undergrad. I wonder say, if someone worked in a council and had an interest in moving into a particular field, could they get a social work or law degree funded? If so, do most council staff go and do a degree, to get maximally trained? Don't see why they wouldn't. Like if they work in the housing department, go get a law degree (just an example).