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Yeahh, I have to agree with this reply. He may be an impressive salesman, but that only seems to make up for the lack of anything remotely interesting about what he is doing for the product now. Sure, it was an innovative concept when it first came out, but after four years of using Blackboard during college, it feels like he missed the boat on improving a product. I wonder if Blackboard is so popular now because of a bandwagon-effect instead of because of being a great product. There's so many things they could be doing to solidify themselves as a truly awesome (and modern) product that they're not. They still feel like software we were using back in 2002. Salesmanship is great, but I wonder how hard you would have to press if you were offering something awesome. Who knows...

Blackboard is shockingly awful, but the people who nominally control the purse strings in education are an incredibly cautious (cowardly) lot, and so for the most part they'll just buy whatever everybody else in their community does.

The teachers who are on-the-ground have very little say in the purchasing process; they're just handed tools and told to use them. Which is why Blackboard continues to have customers, in spite of their shockingly bad product.

I get where you are coming from, but looking at the flip side of your comment shows what a smart businessman he is. While I don't agree with this method either (as I am sure most people that read HK don't) there is something to be said about being agressive and protecting your dominance.