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 in ARR. At that point:

• Your customer base is highly diverse, and not dependent on any whales.
• You have enough reference accounts. You want more—but don't need—more logos, as great as they are.
• Your sales and client success teams are working as a team, as an imperfect but effective engine, and not dependent on a single rock star or two.
• You have a brand, maybe a small brand at first, but a real one. This is a key inflection point in the getting-easier process. More leads come in, more easily. Customers still need to be sold, for sure, but at least you don't have to kill yourself to get into the discussion.
• You can't be killed by BigCo entering the space or the competition. Wounded, yes, but not killed.
• Your product may still suck in a lot of ways, but it's pretty rich with features. You have what many customers need.
• You know the market so well, it's pretty easy to see two years out, not only from a product side, but also from a scaling revenue and team side.

Yes, you'll have to put another plate (or two) on the bench press every six months. And for the few companies that go public, it's a whole new level of pressure like you've never seen.

So growth won't magically eliminate all your worries, but it will get easier. And you'll keep coming up with new—and hopefully better—problems to solve.

Jason's Top 12 Mistakes in Building Sales Teams

I made all these mistakes at EchoSign, and I've seen founders at growing companies make them again, and again, and again. So here's my Top 12 list:

1. You hire a sales rep to sell before you can prove you can do it yourself. You have to prove it's sellable first. And the CEO/founders need to do the initial sales themselves, so that they understand how to make sales work. You can't outsource this.
2. You hire a VP of Sales to sell before you prove you can do it yourself. You gotta prove the process is at least just barely repeatable before you hire someone to turn up the volume and spin the wheel faster. You gotta build two reps that can hit quota before you hire a real VP of Sales.
3. Any of your first two to three sales reps are folks you personally wouldn't buy from. Because then you'll never trust them with your precious handful of leads, and they will fail, no matter how well they did in the last startup.
4. You insist reps #4–400 are folks you personally would buy from. It takes a village.
5. You underpay. The best salespeople want to make money. If you pay under-market, you get bottom of the barrel. Huge rookie error.
6. Not (intentionally) going upmarket faster to Double Your Dealsize. Nothing is an anomaly:
   • If you can get 1 enterprise customer—you can get 10.
   • If you have 1 customer in an industry—you can get 10.
   • The outliers aren't anomalies: They are The Future.
   • Corollary: Target bigger deals as soon as you can—same work, more dollars.
7. Not firing a bad VPS in one sales cycle.
   • You should know subjectively in just a few months—just 50% of the way through your average sales cycle
   • Numbers should increase in one sales cycle—with a keen focus on Revenue Per Lead
   • First few hires should be clear upgrades—and should be made quickly and seemingly effortlessly
8. You ask your VP of Sales to carry a bag for too long. Her job is to recruit a great deal and hit the overall plan, not to sell herself, not mostly. Have her own the whole number, the ARR plan, not an individual quota, not for very long, at least.
9. You hire someone who last sold Nu Skin. This can work later, but not in your first reps. They need to understand how to sell vaguely similar products at vaguely similar price points.
10. You hire because she worked at Salesforce/Box/DropBox/ABC Famous Company. Don't hire them because they worked at a well-known or hot company. Hire them because they can and have closed at least vaguely similar products at somewhat similar price points. Not because they are one of 4,000 reps that sell a product at Salesforce.com, which has $8 billion+ in revenues, a proven brand, and huge infrastructure behind it.
11. You allow any great reps to leave. You should strive for 0% voluntary attrition, not to fire the bottom one-third. That's for boiler rooms. Great sales teams stick together. Great sales teams inspire each other. Great sales teams attract higher and higher quality reps as time goes on.
12. Not doubling the plan. Once the team was (finally) great, we exceeded the plan, every quarter of every year. Always. But … I should have challenged us to do Even Better. I should have pushed harder the same way Parker at Zenefits pushed Sam to answer the question in early 2014: “What would it take to do $20 million instead this year instead of $10 million?”

Advice from the VP Sales behind LinkedIn and EchoSign

If you didn't get a fancy title, would you still work for that CEO?

Brendon Cassidy was one of the first 25 employees at LinkedIn, building their corporate sales team from scratch, and he was the eighth employee at EchoSign, helping to take them from $1 million to $50 million in ARR and an acquisition by Adobe, then spent time as VP Sales at Talkdesk.

Here are lessons he learned from both his success and failures. It's easier to learn from failure. Because what went wrong is obvious and leaves a resounding impression you can't ignore. Learning from success is harder, because success covers up mistakes Enter Brendon: