Need opinions about a work option. I know, I know.

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It's only stupid if it doesn't work
I'd say its common knowledge that I dislike my job. However, as much as I complain I also pursue options to get out of it. I emailed a higher up about an office position and at the moment nothing is open.

Well for the past month or so I have been observing the advertising we sell along the system, at station stops and such. I have a degree in this stuff. It interests me and I know how to do it. At the moment it is contracted out to a huge company, Titan Worldwide.

To put it politely, our contract is being mismanaged. To not be nice, they are doing a shitty ass job. A sophomore advertising major could do better. Ad space sits unused for months or ads sit for months long after the contract is up. How do I know this? I see the blank space where ads should be, and I see ads for movies(at the moment 3) that came out months ago. Two of those movies are already on DVD. Movies that came out in November, don't pay for ad space in March.

A single office employee doing this with knowledge of the system would not only do a better job, but also cost the company less. Contracting companies usually take about 50% of the profit. A single employee usually receives a small salary and 15%. And with my company being my only client and source of extra income(commission), you would be damn sure I would fill every possible spot. With plans to eventually do something like this... The Detroit People Mover - Exterior Train Wraps

So its obvious to me that this is my way out of working terrible hours and probably even make more money although I have never complained about the money I currently make. But there is a problem. I imagine I have to speak with one of the higher higher ups, but NJ Transit does a great job keeping his email and number private. He has a mailbox in the office, but I'm not sure that is the most professional way to request a meeting. How should I go about this?

I have already done a lot of research on doing this. I have even spoken with the media director at the above link, and a vinyl distributor in upstate NY that could handle the wraps and outdoor ads if it were to go that way. So what do you guys think about all this?
write up a proposal, show them the kind of revenue you think you could generate, and what the cost of your services would be. enclose your portfolio/qualifications, and put it all in a spiffy presentation folder or envelope. post it to the boss of your boss - the head honcho decision making guy. sit back and smoke a stogie.
Didn't even think of that. I'd prefer a face to face, but I suppose I could get him interested with the whole proposal then arrange a meeting to completely sell the idea.
first thing they will ask is what connections do you have to sell ad space?
the trick here is to be taken seriously. by default, your boss won't take you seriously. any personal approach will lose the professional appeal that you'd get from a well written and detailed proposal (include recked's suggestion - but without giving away any of or too many of the corners you'd cut or the connections you'd use to make it happen for them).

you've basically got to present this as a whole other facet of yourself, and your qualifications. show initiative. easy to explain why you presented the proposal to the decision guy vs. your boss - he's the decision guy, your boss is just your superv. no hard feelings.

it's business, you have to come across as business - a money maker with a good idea, a great plan, and excellent ROI potential.

edit: return on investment = ROI (for those reading that don't know it).
first thing they will ask is what connections do you have to sell ad space?
I designed the media kit used by a greater Philadelphia area advertising magazine. It's used today exactly how I handed it in to my professor in college(minus price changes). My internship in college was based around this. But all I did was find the contact information for my boss to use. There are no real "connections" in media sales. Especially in the beginning. It's cold calling. Then your "connections" are your current customers(hopefully they never become past customers). But you're still cold calling new clients.

Media sales is not a hard job if you're good at it. If you're not, you will struggle every day.