SaaS Sales Actually Harder Than it Looks, Especially in Enterprise

Most new sales leaders and co-founders think things are pretty simple:

Step 1: Spam enough people to get a meeting with someone who will listen.

Step 2: Feature vomit all the things.

Step 3: (a miracle happens)

Step 4: Revenue!

And to that, I have one question for you: "Are you smarter than Steve Jobs?"

He famously hated Enterprise sales. Why? Just listen:

"What I love about the consumer market, that I always hated about the enterprise market, is that we come up with a product, we try to tell everybody about it, and every person votes for themselves. They go 'yes' or 'no,' and if enough of them say 'yes,' we get to come to work tomorrow. That's how it works. It's really simple. With the enterprise market, it's not so simple. The people that use the products don't decide for themselves, and the people that make those decisions sometimes are confused."

Simply, the user is not the economic buyer. And the economic buyer has other motivations. This simple insight captures the bulk of problems in most software companies today.

"What we have here is a failure to communicate. Some men, you just can't reach." -- Cool Hand Luke

I have a feeling Steve Jobs was a big fan of the Captain in the movie. I can't tell you how long it's taken me to learn and incorporate simple insights like this.

If you have ever found yourself thinking after a demo:

"They surely will go with us, they have so many problems!"

You actually have no idea what business you are in. You are not in the business of solving problems. Any business has thousands of problems, most of which a buyer will never tell you about.

Instead, you are in the business of creating trust. Yes, even in the age of AI this is still true.