The Most Difficult Thing About Building Your First Sales Team

In Revenue Capital

One of the first questions we always get from founders’, centers on what the ideal first sales hire and/or sales team looks like. As a habitual founder who’s taken five businesses to market, all of which were first incubated through founder-led selling, I’ve posed this question to myself and experienced the pain firsthand of answering it honestly.

Things Break

Before ever diving into the composition of those early go-to-market teams there’s a critical understanding that first must take root. It goes beyond sales and is applicable to any early hire – especially when the founder has been ‘wearing those many hats’. When you’ve created something special by keeping many plates spinning in the air on your own, and your standards are naturally sky-high as any successful enterprises are bound to be, the painful realization you simply must embrace is – some of the plates are going to drop.

And they’re going to break.

It’s going to be excruciating to watch. But the lessons learned from that broken pile will be far more valuable than the best sales playbook you could conjure up.

When you’ve spent months, or years even, plugging any burgeoning hole in the dam with your capable founder fingers, the notion of leaving the dam un-manned, even for a moment, is terrifying. Yet, you ran out of digits long ago and if you truly want to build an organization that scales, you’re going to need to ‘find your five’. This is a concept I’ve preached for a long time – to scale an organization to fifty, you need to first find five foundational team members who can extend your vision into every area of the organization. Five turns to fifty, fifty turns to five hundred – the point being that no matter how large you grow, you need to have a central group of high-performers who not only achieve, but breed achievement in others. They will bring their own unique, complementary set of skills, ideally skills that are inverse to your own. One of those key individuals, of course, is your first seller.

Getting one of the important first five roles is just further confirmation of how critical the first sales hire is. But make no mistake: they aren’t a VP of Sales. They aren’t a CRO. They’re a bag carrying rep who punches above their weight class, carries a bit of a chip on their shoulder (having perhaps been passed over for leadership in other organizations) and they are hungry to prove themselves. We’ll go further into the DNA composition of these unicorn sellers in a later post, but the point here is, despite the fact that they are the uncommon, they’re still going to drop the ball.

The upbringing

Nothing in my career has provided as much insight and impact on me as becoming a parent. The parallels between growing a company and raising a human are unbelievably similar. Now, before someone jumps all over me for comparing employees to children, let me qualify this with an example.

Employees. The fact that you care about each team member so deeply and want them to succeed by rapidly imparting everything you know so that they can then leapfrog all of that pain you had to endure to gain that knowledge. Like children, that will likely never happen unless they fall and pull themselves back up on their own. You can guide and you can educate – but at the end of the day that skinned knee or broken arm is going to teach them more than anything you could have hoped to. That’s because we as humans learn the most from experiences – it’s just how we’re wired. The same is true for your first sales hire. Just as it kills you to watch your child fly headfirst over a set of handlebars and into a ravine, there’s going to be a ton of pain involved in placing your cherished prospects, pipeline, and company reputation into the hands of an account executive, fresh out of the wrapper. If you don’t let them fail, get skinned up, and then pull themselves back onto that bike, you’re never going to see them become what you truly need them to be.

Helicopter parents and helicopter CEOs both suffer from the same near-term myopia.

I fancy myself a seller, I’ve carried a bag in my career, and I’ve also run sales teams. In the early days of each business I’ve launched, I played the role of sales for a time. However, even though I have sold, and I like selling, the first hire I normally make is in sales – and once that switch is flipped, it stays flipped. I strongly despise two common things I see happen amongst early sales teams:

  1. Competition between a founder/CEO and their sales team
  2. Long ramp up periods

Allowing a sales hire to jump in headfirst and fail fast solves for both. After all, you’ve made an investment into this individual, they’re not here to be your note taker on calls. They’re not your EA. They’re one of your five – and their ability to fulfill that destiny depends in no small part on your ability to get out of their way.