This all looks like a lose/lose to me. A COO, no matter how well you know them, is going to run the political risk of signing off a services spend on someone with relatively little experience and (critically) as a contractor no accountability. In the same instance, the best you would achieve is to win a piece of work (2 day proof of concept) which would be too high on cost to serve to have any margin, so now you look bad at your current company. I could go on. This is a truly bad idea. Take Bushy's advice - get your manager involved.