From Impossible To Inevitable

Chapter 9Learn from Our Mistakes

What makes sales scalable? Where do people fail? What problems can you solve before you run into them?

Growth Creates More Problems Than It Solves—But They Are Better Problems

A top engineer from EchoSign, who had strong experience in growing both consumer Internet and enterprise technology companies, told me a while back that the number one reason he disliked SaaS/enterprise selling: It never gets easier.

His point was, once you solve the problems for Big Customer #1, then you get 10 more Big Customers, which mean 10x more problems. Then 100 more customers, which is 100x more problems. It gets worse, not better.

A fair point for the development team of a technology company. And especially true if you have a consulting or services business.

But one of my top learnings from EchoSign, going out to all you technology startups and founders out there: it gets easier in other ways. Once you get past 50 employees, it gets a lot easier. Once you break through $10 million in ARR, it gets a lot easier. And once you break through about $15–20 million in ARR, it gets truly, dramatically, a whole lot easier.

It's not that it gets any easier to grow, or hit your plan, or make your investors happy. That stays just as hard. And competition gets harder as you cross this point—your competition sees it, and tries harder. And more enter the space.

But much of the operational pain, especially in recurring revenue SaaS companies, seems to go away around $10–15 million ...