Is it a good idea to go around the CIO?

It’s a smart idea to ask around, so you might want to ask the marketing people (or)  the strategy people. You might have a connection with the CFO, who’s often the chief strategy officer as well. It’s good to understand from many aspects, but don’t upset your primary decision maker and buyer by end-running him.

If you’re thinking of yourself as a Shadow IT supplier and you’re thinking you’re going to end run the IT function, be careful because you might upset the (key) buyer.