How to Close the Big Sale

As an entrepreneur, you have two big, important jobs. One is to create a killer offering your customers can’t live without. The other is to sell. And the most successful companies, as Sequoia Capital partner Jim Goetz recently told attendees at TechCrunch Disrupt, sell to the $500 billion enterprise market.

Unfortunately, when it comes to selling to other businesses, we solution providers tend to lead with the answer, rather than first asking questions that illustrate the problems we’re trying to solve. We also have to deal with each prospect’s organizational politics. It’s easy to get lost.

Rani Hublou is a technology entrepreneur and corporate executive with a track record of success in selling big.  Right now, she works with me at IBM. But she has also led B2B start-ups such Icarian, BroadVision and most recently PSS Systems through successful venture fund-raising and acquisitions.

Rani believes that enterprise selling is both science and art. The science requires a systematic approach to understanding the present state of your target’s business. The art lies in your reaction, and in how you lead others to see that you have a viable solution. Here are Rani’s tips for perfecting the art and science of the enterprise deal. 

Paint a picture for the top

The top of the business--the senior leadership--is where you will close your deal. These are your decision-makers. Often, as salespeople, we want to talk about our offerings’ unique features and functions. Guess what? The C-suite and their direct reports care about two things: time and money. They need to hear you tell a cohesive story that shows you understand their current situation at a deep level.

Only when you prove that you know their business will they trust you to help. When you talk about your solution, you paint a new picture: of where your client could be in the future, by using your product or service. In that picture, you quantify how your offering will enable the customer to reach their strategic goals. Your story should focus on moving them from where they are to where they want to be. Use trending data to show why your solution is important now and why waiting does not make economic or competitive sense.

Know when bottom-up engagement is enough

It’s easy to get lost in bottom-up selling. Don’t. Your bottom-up activities should focus on information gathering so that you can accurately relay your prospect’s current situation to the top brass. Of course, you also need to build relationships with these folks. Many of the operational people you will talk with are also influencers, and the decision-makers will turn to them before signing on the dotted line. Make sure the version of reality you paint for executives is the same version their staff would paint. And be humble. You do not live their business. They do. 

Know what's at stake

If it’s true that women are more relational than men in our decision-making and interactions, then we should be naturals when it comes to selling. Use this opportunity to take that relational behavior to the next level.  When you are selling, think about each person’s “stake” in your sale. What would each person gain from your product or service?  What would they lose? What pain are you selling to? How can you uniquely remedy this pain, and what happens if you do not? Let this understanding guide your conversations.

Use the yo-yo as your indicator of the educational process

An enterprise sales cycle is full of ups and downs. Sometimes the pendulum swings multiple times in one day, especially when you are closing the deal. You should expect that. When things are up, reflect upon what’s working. What messages are sticking with your buyers? When you see the decision-makers wavering or putting on the brakes, remember that sometimes the conversation begins with no. “No” is just a word, and in your case, it’s an indicator.  “No” might mean that you are hitting on a pain point, one that requires a bit more probing.  “No” might also mean you are missing the mark.  And, yes, “no” might also mean “no;” part of great selling is knowing when to walk away. But chances are, “no” is a great opportunity for you to educate your