Here's a three-part (1, 2, 3) article giving a good overview of the process of selling to large companies, why it's such a pain, why startups are at a natural disadvantage when compared to larger competitors, and what they can do about it.
The whole series is full of useful information, so I'll quote just one paragraph and let you read the rest on the Favo.rs Blog.
One of the biggest mistakes startups make when selling to enterprise customers is to focus almost entirely on optimizing price and features for those customers. While price and features are important for the enterprise customer, chances are that you're within the range of acceptability for both of these. Where you fail as a startup, however, is passing the enterprise customer's "Will this product f&%# up my systems?" test. In other words, is the product or service you sell reliable in its own right…and is there the risk that it might mess up other critical systems already in use at the customer? Believe us - nobody wants to be the person who brought down their entire company's network because they purchased faulty software from an unknown startup. And, as they say in the industry, "Nobody ever got fired for buying from IBM." So how do you alleviate this fear on the part of your potential customers? You need to provide credible risk reduction in the form of customer testimonials and passionate dedication to customer service (fix bugs fast!). It also helps if you can partner with a larger organization that already has an existing relationship with the customer to bring your product in (hey, you might even try partnering with a larger competitor). Ultimately, however, you can't get over the fact that the customer will need to take time to become familiar with your product, either through their own use or hearing about others' use, before they have a comfort level that it won't cause serious problems. In our experience, this can potentially add months to a sales cycle depending on the size and risk adversity of the customer in question.
If you read this far, you should follow me on twitter here.
