Disclaimer: I work at Instructure, the company that makes the LMS Princeton is moving too. Opinions are my own, etc First things first, Blackboard is some of t

Disclaimer: I work at Instructure, the company that makes the LMS Princeton is moving too. Opinions are my own, etc First things first, Blackboard is some of the worst of enterprise software and a huge part of why they have lost so much market share is not only because they had a difficult and obtuse to use product, it is also because they were extremely aggressive in buying out any competition and EOLing their products and forcing schools against their will onto Blackboard. And I think this is the bit that is often the case about the worst enterprise software is the it gets to a point where customers are so entrenched that the company behind the product has market forces that drive it to grow through unhealthy means that are often hostile to customers. To his conclusion about all software tending towards these same problems, I can't agree more. It is a HUGE challenge to continue to deliver software that remains easy and friendly to use in light of the real need to add real features. You simply can't just ignore the market that thinks differently about a given problem and the workflow to solve it. I think the right answer to this problem is not just really great product and UX (though that is critical), the real challenge is to figure out the underlying technology platform and engineering process that makes it cheap to build new features and compose them together without the complexity becoming overwhelming for your average engineering team. From what I can tell, this sort of architecture looks vastly different from how most software is started and how we think about software in general. Making that transition is one of the hardest things to do in engineering and it is what sets apart companies who continue to deliver well liked software and those companies that tend towards being defined by worst tropes of "enterprise software"