Marketing to enterprise customers

Here are some thoughts:

1. The larger the business, the more they have to "justify" the money. That means ROI.
2. People with the pain usually don't have the ability to pay to fix it (Jake's point above)
3. People's jobs are on the line with big purchases, so spend lots of time getting them comfortable that you'll make them look good (promotion) without risking big failure (firing).
4. "Big companies" are still run by humans, so it's still about human relationships.
5. The sale will involve different people with different needs and different worries. Listen to each individually; don't think the sale is won on a single argument.
6. They expect big support and long trials, but if they purchase they'll pay for that. Just make it clear that you expect it.
7. Getting maintaince payments over 20% of original is neigh-impossible, so instead make the up-front cost more.
8. The "purchasing guy" has no power but will pretend to. Do not give in to purchasing. Negotiate prices with the actual user and ignore the guys from accounting.

I'm going to assume that you're referring to selling a packaged application to enterprise customers (vs "enterprise software", which everyone should stay far away from SRSLY TRUST ME ON THIS ONE)

The thing I have found consistently the most infuriating about marketing to the enterprise is how the person you're selling to (that great guy at the trade show, the "Contact Us" lead from the website) often doesn't have the authority to make a purchase. And they may not even realize it.

We don't really have too much of a problem generating leads, our frustration starts once we have the leads and start to sell. We use a process called ORDER and is based on the book Let's Get Real Or Let's Not Play by Mahan Khalsa. Basically it goes like this:

(O)PPORTUNITY/ISSUES - First we "put aside our solution" meaning we have a general discussion with the client about their issues instead of selling them on our product. Issues are "measurable" problems they are looking to solve (improving efficiency, reducing paper) or results they are hoping to achieve (improving profitability). We can use this information later in the sales process. This can be a short, 15 minute to 1 hour conversation.

(R)ESOURCES - What is their budget? Are they willing to devote full time people to this project? If they want something so bad what has held them back in the past? This is where we try to determine if they can afford to use us and if they'll commit the personnel necessary to ensure a successful implementation.

(D)ECISION PROCESS - Next you have to figure out some way of documenting their decision-making process. This is one of the hardest things to do because people understandably don't want you to know their company's inner workings, and/or in many cases don't realize they aren't a decision maker. Be sure to identify all the key players and their role in the process. A key metric is that we never want to present a solution to anyone whose exact criteria for judging us is unknown.

(E)XACT SOLUTION - The "pitch." Understanding all of the above, we present a proposal to the client, generally in the form of a product with pricing information. DO NOT DO THIS BEFORE THE FIRST THREE STEPS ARE COMPLETED! (note, in your case this is less relevant because pricing is transparent)

(R)ELATIONSHIP - This is where we finalize the relationship by signing a contract, etc, delivering the product, etc. This part of the process must be carefully managed in order to ensure the customer doesn't back out at the last minute.