[jeremymims]

There's certainly innovation taking place in enterprise sales, but don't discard the "old school" just because it isn't new. Many of the largest companies you can think of are "old school". Traditional enterprise sales is high touch relationship building with millions of dollars at stake. And it isn't the cold call BS boiler room stuff that people think of when they think of enterprise sales.

The best enterprise salespeople become great friends with their potential clients. They know what schools their clients' kids are going to, where they went on vacation, and who they need to introduce them to. They know when a client's birthday is and which restaurant she's eating at to call and pick up the tab. They know how a client takes their coffee and what their favorite drink is. They show up with hard to get theater or game tickets. They're sincerely invested in the success of the client. The client isn't a "mark" to them. Clients are friends and you'd never do anything to hurt your friend. In many ways, a great enterprise salesperson becomes the advocate for your customers inside your company, pushing you to create a better product because they never want to let their friends down. Great enterprise salespeople know how to ask for money because they understand the value they're delivering and also when to comp something. They know how to say sorry and they know how to keep a valuable customer.

The fact is that this kind of selling is hard to scale. However, it's worth it at less scale because the account sizes are usually quite large. Your best enterprise salesperson is like a Zappos account rep on steroids. Clients feel great and they give you the chance to build a product that they love and recommend to other large account holders.

This isn't for everyone. You should probably be in a market where you can make $100,000 per year from a client (you'll probably be making the client $500k+ per year and you'll need a product that lots of clients need) to employ an "old school" strategy. And it should be said that there are bad enterprise sales people. They'll abuse your clients, make you develop the wrong features, and some won't sell a damn thing because they're better at selling themselves than they are at serving clients.

Great old school enterprise salespeople combined with a top-notch product is a killer combo. If you find a few techniques that help you sell more, that's great. Just don't be in a hurry to avoid building a real relationship with valuable enterprise clients. If you're easy to switch to, you're easy to switch from.