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Tim Armstrong, Google's head of North American advertising and commerce, is tasked with turning Google's $1.65 billion money pit cum legal headache, YouTube, into a profitable enterprise. Since the departure of the online video-sharing site's former moneyman, Shashi Seth, ideas ranging from affiliate links to iTunes to sharing revenue with third-party sites that embed the limited stock of professional videos, have been floated. But the real problem seems to be an amazing number of bottlenecks any deal has to go through, the Wall Street Journal reports:

Some YouTube advertisers, for example, had to pore over three separate legal contracts. Before Google salespeople around the country could propose certain deals to YouTube advertisers, they first had to get approval to do so from a temporary worker in California. And lacking a fully automated billing system for YouTube, Google staffers had to calculate some bills manually.

I'm sure Google would rather just automate the process and provide a link to the relevant documents — because it's apparent any business system at the company involving humans is at least as inefficient as it is anywhere else, if not more so. Problem is, sponsors looking to spend big on a campaign want to shake hands on a deal with a media buyer who's wined and dined them and let the lawyers and secretaries hammer out the boilerplate, not click through Web forms before paying for a seven-figure buy with Google Checkout.