Act Appropriately Up To the Cxx Level...
How do you know you can 'act appropriately up to the Cxx level'?
I ask, because that's a really confusing thing to lead off a list of technical skills with. If you're reporting directly to Executive Management then you aren't an 'IT Generalist', you're an 'IT Operations Specialist' or 'Special Projects Specialist'. Your technical abilities will account for about 50% of your value and your communications abilities will account for the other 50%.
You're going to be competing with lots of technically competent candidates, so unless you're phenomenally exceptional technically, you're going to get lots more traction if you focus on your communications and sell your value to potential employers in a way that directly communicates how you add value to the company. Most of your fellow candidates will be completely forgotten if you explain what you will add to the future of the company instead of going on about what you added to a previous company which obviously wasn't appreciated and/or valuable. Your job is the future, not the past, that's the same job the people who hire you have, so it's good to communicate on the same plane. Generalist isn't anywhere on that plane either.
This next bit is good for more money, but reduces your prospects if a hands on, technical role is where you want to be. However, if a senior technical position where you'll be communicating directly with senior management is your goal it's the best way to get your chance to sell yourself.
Identify your business specialty and/or industry and support that with your technical abilities. Everybody you're interacting with is going to have technical abilities. If you focus on those you're effectively setting up a competition between yourself and any other candidates with the same skills. Who has 'the best' or 'the most' among competing candidates isn't anything you can control and reducing variables is going to be the key that gets you the opportunity to justify your rate. Let the others fight out who is the last true COBOL expert on Earth, or whatever.
While those guys are debating the merits of various query structures you get to walk in and get the job because you talked about how you excell at accelerating new business unit growth by creating an invisible, seamlessly integrated IT environment that delivers business services that 'just work' by focusing on the needs of the users and the demands of the business through technical excellence and communication. Or some shit like that (the above is an off the cuff garbage example, don't use that in practice. Be specific about what you do :).
You're getting hired to serve the needs of others, it's on you to figure out how your technical skills best translate into meeting and exceeding those needs and communicating that in a way that's useful and, crucially, noticeable above all the noise. I'll give you a hint though, your skills are a statement of what you have, unless you're interviewing to be robbed the only thing that matters is what you are going to give to the future. Your skills are like a tool inventory, and worth fuck all by themselves. How you're going to use that inventory is all that matters.
I got my big break when I was hiring myself out as a professional interim executive. Mostly for hedge funds who were 'realigning' (destroying) companies. They needed somebody to go in and determine what should be kept and amalgamated with other things, and what should he sold off. Then I had to turn whatever was left into a functional, money making, business. That's about as 'generalized' as you can get. I reorganized everything from small generic pharmacy products manufacturers to two firearms manufacturers, a laboratory equipment manufacturer and finally a network equipment manufacturer where I was offered a permanent role as COO where I was responsible for getting 31,000 employees organized for an IPO six years later and coming back later to help with the acquisition of that company.
That's relevant here because at no point was a selling myself as a 'generalist'. If you're not a technical specialist that doesn't make you a 'geberalist' that makes you an, as yet, unlabeled business specialist. You just need to find, or create, a label that let's others know what you do. These days I'm running my own little specialty manufacturing business and I'm on the board of a VC firm in DC. I've got an enormous database of business specialists I call on to put inside our portfolio companies to ensure success. Many of their day rates are in $2k+ range and the reality is most of them are 'generalists', but there's nary a single 'generalist' search parameter in my database. The system is all business oriented and organized by business specialty.
Your technical skills are nothing more than what you use in your specialty work. You need to define your business specialty. The career path and money you're looking for are there.