Here's how I would apply for an IT job at this stage in my life. I do not want a job again, but here's my general impression of how I would go about it. My guess is the approach isn't effective, but who knows:
Dear Hiring Manager,
My decade of experience in IT and 25 years of managing employees, clearly qualifies me for the position, but I wanted to touch on something you may not have considered. Running a small business for the last 16 years has provided a perspective on IT that I'm sure few of your IT employees possess. You see, I dislike technology.
I am not enamored with technology, nor do I wish to burden your company with a bunch of soon to be useless gadgets and computers. In small business, you quickly learn that IT is a cost center, an expense that you wish was unnecessary, and to the extent you can make it unnecessary, you do that. Clever technology is not so clever when you're troubleshooting a computer on your office floor on a Saturday night, rather than being with your family. What I'm saying is technology needs to be applied intelligently, and most often in IT, it is not. IT experts are often on to their next gig, long before the return on investment fails to materialize.
As your new IT professional with a small business background, you hire a skeptical expert. You hire a technologist who doesn't slap a business case onto a shiny piece of new tech, but starts with the business case. I want to learn about your business and how technology will advance it, improve it, make it better in every way. I am also fully satisfied to let the "trains run on time," and keep your operation in tip top condition without change. I have nothing to prove and I'm not obsessed with the next tech gig or building the resume.
In short, I wish to partner with your organization, make it my own, understand what makes it tick, and when necessary, and only then, bring it the latest technology to propel it forward. For sixteen years, I applied just the right amount to my business, resulting in a modest 10% a year growth rate, while technology took a back seat to people. A good IT opportunity should have a solid business case, with a thoughtful cost-benefit analysis and prompt return on investment. I can't promise to make your IT a profit center (although I've seen that done), but I can make it a less painful center of cost, while focusing on what matters to your company, the people.
I would be happy to discuss this position and your needs in more detail.
Ex IT Guy