As a product person in the enterprise space, I think there's a lot of good things in this article. BUT, there's a couple of things that I think reflect Steven's background at Microsoft and are common assumptions in the Enterprise space that no longer hold universally true.<p>- There's a lot of talk about "IT" as a group that you sell to, which by and large only still exists at the highest end of the market, and even then largely as a group whose buy-in you have to get past in order to complete the deal. Many technologies these days are sold directly to the LoB, and IT's only involvement is a security audit, data recovery strategy, and integrating the new app into SSO.<p>- The downside of this is that many, certainly not all, organizations are a lot less mature than they used to be when it comes to rolling out technology. After all, if all you have to do is log into a web portal and start doing things, what prep do you need? Consequently, your implementations will be a lot more successful if you can show up and <i>tell</i> prospects how to roll out your software, or migrate away from a competitor<p>- I find that a lot of these organizations are less mature when it comes to understanding "roadmap vision" - they're a lot more aligned to, "What can I do now?" and "What will I be able to do in six months?". There's nothing wrong with that, but selling vision that might represent an aspirational dream for three years out can conflict with the short-term vision of the stakeholder<p>In general, I think the disconnect comes from the fact that IT in a lot of organizations grew to a sufficient size that the justification for (some of) their existence was implementing and managing the implementation of enterprise software. To do this they built processes and procedures that mitigated risk, helped them plan, migrate effectively, train people, etc.<p>Those same processes also created jobs where the sole purpose was to justify their existence and increased overall complexity.