The players in the industry that went after enterprises are doing well, the players that stuck to selling mostly to individual customers are having a rough go of it. Udacity definitely had some big enterprise deals with their specific nanodegrees, but it never looked like they became an enterprise sales company from the outside.
I believe most marketing departments (along with people trying to make a name for themselves) have massively cranked up the amount of free content they pump out in the last few years. It is making it terribly difficult to become big in the education space while selling to the masses.
Enterprises, on the other hand, _really_ want to lower their salary expenditures through training and will happily throw money at a company like Pluralsight to train up new employees. For what its worth, I think they're correct that training can drive down payroll costs. But the company I worked for was acquired by Pluralsight, so there's some bias.
The problem is more the overall devaluing of content prices by consumers generally. Especially absent much in the way of certification value for most people, that places a real ceiling on how much you can charge. I might pay something in the neighborhood of book pricing for an online course (or I may take one of the numerous free alternatives). But I'm unlikely to pay triple digits and I certainly won't pay thousands of dollars.
Keep in mind they had a deal with Georgia Tech's OMSCS, but something went awry there too.
It’s not hard to see why: GT said recently that through 5 years of operation the OMSCS has made $14M for the school. That’s wonderful from their perspective, but that’s a total disaster for a VC-funded unicorn company.
"Last year, Udacity generated about $90 million in revenue.
Even as Udacity slashes costs and headcount, it’s trying to expand its enterprise business, which has had recent success. Udacity now has contracts with 60 enterprise customers, including AT&T and PricewaterhouseCoopers. Airbus and Audi recently signed on, as well."
I don't know what this looks like as a business but I can imagine it's easier to sell a relatively modest number of business subscriptions than it is to beat the bushes for a lot of retail $10-50 courses.