Does having a background in IT Support benefit an executive IT leader?

I believe the higher you are in the corporate chain the more customers you have to serve and satisfy. Every IT leader should work for his direct and indirect reports in a sense that he/she needs to support them to be successful in their roles so he can be successful in his/her. Having that in mind, an experience in support or a mindset of one surely is greatly beneficial

Absolutely. It exposes one to a wide variety of problem scenarios, personality types and to think fast on your feet. The experience helps to create or reinforce active listeners, teaches problem solving and most of all the meaning of the word empathy.

The way I got progressively bigger jobs was through support and customer service. I was known as the guy that can help you fix your desktop, or connect to the printer, etc., and I wouldn't put anybody down like, "You're so stupid, you don't know how to print." I would sit there and just listen while they went on about all the things they tried doing. Then I'd push two buttons and they could print. 

I just tried to be super nice to everybody when they brought me their laptop to fix it. I'd make sure I wiped it down and cleaned it, and made it look better than when they got it before. And they appreciated that. The only problem was that as we got more IT people, they would all still call me directly because they wanted my help. But the positive side effect was that as these sales folks or execs went to other companies in need of an IT guy, they'd say, "I had great experience with Todd, we should bring him in here."

Help desk is where I realized that pretty much every single employee within your organization is your customer, because if your NPS scores are low then you can answer why it is low, what kind of a service you’re providing and why it’s not on par with industry standards.