[Rickasaurus]

I work for a company that has only tens of clients (banks) but each pays us in the hundreds of thousands to millions range, an extreme example of B. Just one of these customers takes up to a year to acquire.

On the plus side, things can move more slowly and in a well thought out way. Also, there's no worry around your usual "web scale" issues. There's also a lot of freedom around exploring new ways to do things because of the slower pace.

On the down side, the customers sometimes put insane requirements in our contracts. Security audits, source code in escrow, huge amounts of insurance, long weekly meetings. The culture of bureaucracy bleeds if you're not careful. Also, income is lumpy and one client can end up costing more than they're paying you if you're not careful.

All in all I think it's the best kind I've experienced so far. That's probably because my employer has done a great job of insulating me from the down sides though :).

[bmelton]

Having been on both sides of the Fortune 100 sales cycle, it was always a fun game, as a buyer, to see how close we could get to being written off during the courtship process. Drinks at lunch are the norm, but maxing out the champagne costs, getting box seats at games, etc.

Once (if) the sale closed though, it was down to business, and doing our damnedest to maximize both our time and the vendors. I've never worked with or for banks, but I can't imagine them being TOO terribly different from federal IT, so I definitely sympathize with your plight. It seems as though all they really want you to do is acknowledge, in every way possible, how happy you are to have their business, and how lucky you are to be in meetings with them all day every day.

[Rickasaurus]

Funny thing is, we're a 25 person company and most of our competitors are much much bigger. However, they're so slow, inflexible and outdated tech wise that we just blow them out of the water with our offering (we charge 2-5x the going rate).

The biggest insight that contributed to our success came from our CFO who realized that big corporate IT is where dreams go to die and that we should route around them as much as is possible.