I thought I'd let everyone reading this thread that AJ Kohn just published a new post that directly addresses this very issue: http://www.blindfiveyearold.com/new-ways-to-track-keyword-rank
Dr. Pete, AJ's post echoes what you said in the comments here exactly. You said "1) Try to come up with a tangible metric, like average ranking across a set of keywords, or total organic search traffic, or total queries, etc. that you can show the boss is more connected to actual traffic and sales. If you can get him to accept a metric that's more on your terms, it'll be better for both of you."
AJ's suggestion "A rank index is also a great way to report to C Level executives. These folks understand index funds from an investment perspective. They get this approach and you can steer them away from peppering you with ‘I did this search today and we’re number 4 and I want to be number 1′ emails.
It becomes not about any one term but the aggregate rank of that index. That’s a better conversation to have in my opinion. A rank index keeps the conversation on how to move the business forward instead of moving a specific keyword up."
HIs post includes step-by-step instructions. Being the Excel moron that I am, I'm going to have to spend some time creating the suggested pivot tables, but hey, I have 6 months right?
The timing of this post was pretty spot on and I appreciate you all for giving me some direction on a situation that could have been not so productive.