The senior sales hire that will DESTROY your startup

You’ll believe this salesperson to be your startup’s savior. He’s got an incredible Rolodex and 30 years of relevant industry experience. Let’s call him Charlie Charlatan.

Charlie knows how the game is played in the big league. Yet, he chose to play with you in little league. Why? Oh, he can explain sure! Reasons you’ll enjoy listening to: he believes in your vision, he can see the potential in your idea. He thirsts for the speed and spirit of a new startup.

You’ll meet Charlie when you need him the most: early on when your startup is struggling to find product/market fit, struggling to grow consistent revenue and sign up new paying customers.

These are the kinds of thoughts you’ll be pondering in your mind:

• Why is sales so difficult?
• Why don’t we have more customers?
• We need someone who can close more and bigger deals.

There he is: Charlie, your knight in shining armor, ready to slay the monster that’s holding you back from explosive growth.

If this sounds like a cheap fairy tale … that’s because it is!

Here’s what will happen

Charlie will join your team, and he’ll negotiate as much money and equity out of you as you’re willing to give up. (But hey, that just shows what a great salesperson he is, right?)

Charlie will start calling, reaching out into his network, building a stellar pipeline. You’ll hear him talk much about prospects, leads and opportunities.

All that’s needed to turn these opportunities into customers is …

• More and higher quality sales materials
• Expensive steak dinners
• A “slight” tweak to your product, an added feature, a different UX (Charlie knows what will make prospects buy because of all the conversations he’s having, so of course you should listen to him.)
• A redesigned website
• A better drip campaign
• A new piece of sales or marketing software (“Yes, $15,000 looks like a lot, but that’s just the price of doing business, trust me on this.”)
• Hiring an outsourced lead generation company
• Spending $60,000 on AdWords
• Feeding a unicorn with magic barley on full moon nights

Charlie will initially make little asks, reasonable requests, but they’ll increasingly turn into bigger and bolder demands. After all you’ll have invested already, you're not going to suddenly pull out. All of it would have been wasted.

All those hot deals he’s working on take forever, and never materialize. “It takes time to close those massive deals”, he’ll tell you. Which isn't wrong, but you need to be involved, to have a read on the temperature of the deals yourself and not just trust someone else’s judgment at the super early stage.

At one point, most likely when it’s already too late, you’ll realize: inside that shining armor is not a knight, but a black hole that devours all your startup's resources, until there’s nothing left of it. Charlie will be on to the next startup, peddling his counterfeit sales expertise.

Why do so many smart founders fall for Charlie Charlatan?

For the same reason smart people have fallen for con men's schemes since hundreds of years: they want to believe them! The shysters’ promises sound so good, we desperately want it to be true. That desire overrides all the sophisticated processing going on in our neocortex.

Even Charlie often believes his own bullshit. From his point of view, it’s always forces outside of his control—the founders, the market, the VCs, the other reps, the incompetent VPs, the CEO—that prevent him from the breakthrough success he’s chasing.

The simple truth is: a truly great, successful senior salesperson won’t join your scrambling little startup. That salesperson would earn hundreds of thousands, maybe millions of dollars a year, without the stress and uncertainty of startup struggle.

But shouldn’t you hire people above your own weight class?

Common hiring advice is: Recruit someone who’s better than you doing _____ (sales/product/management/marketing/etc).

It’s great advice, but there’s an important clause that needs to be added: Recruit someone who is a little bit better than you at doing _____.

Hiring people below your own skill level is fairly easy.

Hiring people in the same level as you is hard.

Hiring people who are a level above you, a bit more experienced, a bit more skillful, a bit better at what they do than the things that you are doing, that’s crazy hard.

But hiring two or three classes above you? Impossible.

If you’re a scrappy little startup with a handful of employees, you won’t be able to recruit Tim Cook as CEO, and you won’t be able to recruit a top VP of Sales.

The one exception

If that VP of Sales rockstar is someone you’ve known all your life. Your brother, your mother, your cousin, your childhood friend from school? Different story.

But anything other than that? Almost certainly a pipedream. You’ve got better chances of success driving to Vegas and betting all that equity and money on red.

Reality check

If you ever find yourself in a situation like this, and you’re still tempted after reading this, you’re too scared to lose the great opportunity to bring that sales rockstar on board, put your Charlie to the test.

Don’t hire nor reject him yet. Instead, say this: “Hey, Charlie, before you leave your amazing job and join our high-risk venture, let’s make sure that this is really the right opportunity for both of us. I know you have this incredible Rolodex, deep industry knowledge and valuable experience. Let’s close one deal together before we do this.”

That’s it. If they are really that excited about joining your startup, it’s not too big an ask. In fact, it’s in their own interest. Have them close a deal for you.

Not promises, not a pipeline, not a partnership proposal. Have them bring in real revenue from paying customers.

Can they do it? Great! Disregard everything I told you and hire them. (Also, send me an email to tell me about it, I want to hear THAT story!)

What should you do instead?

Now you know that when a senior salesperson wants to join your startup, you should turn around and run the other way. But where should you run to? That still doesn’t solve your problem, does it?

Sales are still slow.

You still need bigger deals.

You still need more customers.

So what do you do? I’ve outlined the complete gameplan in my post on sales hiring for startup founders.