Every news organization that I've talked to that's used Ellington loves it. If they want to seriously make a change for the better in an industry dominated by antiquated CMSs that users hate, they need to open-source it. Hopefully they make the right choice here.
"We think a lot of our Ellington product and think it’s one of the tops in our industry"
Frankly, I don't think so, and that's probably the problem.
I could be wrong but most companies management that got a baked CMS think they got the most powerful, frikking awesome, and it general it's just a soup of unmanageable legacy code.
Of course there is a lot of other problems that could spring like a bad sales teams, but if the platform awesome ido not see why it should not be striving since it has been online for so long.
Echoing the other poster here, I think it's naive to assume that it's failing due to a low-quality codebase for a variety of reasons. It's largely the same developers that brought us Django, but more to the point, even if it had the ugliest code base known to man, that wouldn't impact sales.
What they're likely running into is in trying to compete with 'good enough' blogging platforms. Ellington is positioned awkwardly outside the high end of consumer-grade blogging and well below the low end for most enterprise-class CMSes. The customers they have are elephants, and unless you have a specifically tailored sales team, elephant hunting is a very hard business to be in, especially for the kind of product that Ellington is, wherein it is not solving any core business needs for anybody except, probably, other newspapers and journals and the like.
Honestly if Djang is any indication of the development skills of the team I highly doubt the codebase is a huge mess. There are not many organizations where the development of an in-house tool spins off a high quality framework that becomes a mainstream tool.
The issue with Ellington has always been it's closed source nature. You make a lot of money from people who install, setup, and use your CMS/app/whatever who need a support contract later on.
If you have to pay up front, you're much more likely to go with something like Wordpress.