It is a lot easier selling to senior management than the people who influence their decisions from far away. They make the decisions, don't usually waste your time, and will make things happen.
However beware of books like Selling to VITO. You don't need to start at the top. The ideal place to start is somewhere. Maybe the entry point is that technical guy in the cubicle who is the only person in the company who knows what's happening on the website. Everybody knows it.
In other cases the CMO is the right place to start. He was brought in to change the culture and get results. You better get him engaged or risk spending years wasting effort and time.
However you have to be ready to engage the CXO level. I subscribe to Seeking Alpha alerts and read quarterly earnings transcripts. That's the only language people in these positions care about.
I met a sales trainer who told me it is not necessary to know the technical issues but rather the business impact the product delivers. That's great in concept but the reality is that critical people on the decision making team will have no respect for you if you don't know at least some of the details.
My experience is to never claim true technical expertise but learn the language and the issues well enough to have an intelligent conversation with the experts.
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