Dear SaaStr: How Do You Become Successful at Enterprise Sales?

If you haven’t done enterprise sales before, the biggest thing to understand: you can do it. But, you’re going to have to hustle. Really, really hustle.

Many founders want the customers and leads and users to come to them. They want to focus on the product, then on the funnel, A/B testing, optimization, SEO, SEM, etc. etc.

That’s all great, and for self-service business, that’s most of it. But for enterprise sales, you’re going to have to get your arse out of your home office and go close some real live human beings:

  • Listen — often in person. That often includes flying somewhere. It may include flying a lot of places, in fact, that you don’t really want to go.
  • Learn your prospects’ business processes in detail, and how your product enhances them. If this is boring to you, you will fail.
  • Learn how your potential customers will excel in their companies through your product. How can you help the career of the person buying your product? It’s not just about your fabulous UI/UX.
  • Make, or don’t make, commitments to future development and features to meet their needs. Your product will always be deficient in some fashion in the enterprise. Always and forever.
  • You’re going to have to learn how to not take no for an answer, how to beg for a meeting, and how to ask for money and a check. This is really, really hard if you haven’t done this before.
  • You’re going to have to learn how to map out and sell to multiple stakeholders. The person you first talk to at a prospect is rarely 100% in charge of the buying decision.
  • And internally, you are going to have to manage and hire salespeople. Some will be great, some though won’t and will just take your money and will prove extremely expensive. You’re going to have to invest A LOT of time here. You can’t just hire some magic “VP of Sales” with 4 years of experience and have him/her scale the business. Instead, if you do that, you’ll actually end up with less sales than before.

Want to do bigger deals?  Even deals much above $3k ACV?  You’re going to have to learn to do all, or at least most, of the above.

A related post here:

Dear SaaStr: At What ACV Can We Afford a Sales Team?

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