I hung my sales hat a few years ago and transitioned into the world of IT (Moved over to the dark side? or the  bright side? depends on your perspective).
As I interact with friends and peers on either side of the Sales/IT "divide" one issue keeps cropping up all the time -
What's the best way to "sell" to a CIO?
Well, for one I tell them the crux lies in the SOLUTION.
CIOs are not looking for just products or services; they are looking for SOLUTIONs to business and technology problems they have to help their stakeholders/value chain partners address.
And what exactly could be your SOLUTION?
S - Solve don't sell.
O - Orient yourself.
L - Leverage "connections".
U - Understand the CIO's pain points.
T - Talk to the CIO's ego/passions. 
I - Individualize the message.
O - Observe, Introspect, Correct.
N - Nimble and Responsive.
S - Solve don't sell.
Pretty self explanatory. Present your product/service as a solution to a problem the CIO wants to address.Which means you need to have a good handle on what those problems are and how your product/service can address them.
 O - Orient yourself.
Know the lay of the land. Try to understand the dynamics of the organization and the interplay of the various decision makers/ influencers. Do your homework.
L - Leverage "connections".
LinkedIn is your friend. References can help get your foot in the door.
U - Understand the CIOs pain points.
Helping to alleviate the pain is the best way to get a share of his/her mind.....and then a share of the organizational wallet.
T - Talk to the CIOs ego/passions.
Does s/he have a particular passion? Never hurts in positioning your product/service in alignment to that. 
I - Individualize the message.
Ditch the cookie-cutter. Your message should be individualized for the specific CIO and his/her organization.
 O - Observe, Introspect, Correct.
Be flexible to course correct based on the response and changing situations.
N - Nimble and Responsive.
CIOs requirements can rapidly evolve/change based on their business stakeholders requirements. Be prepared to turn on a dime. 
With the SOLUTION in hand, it should be an easy sell.
Happy Selling!