Startups have a shortage of salespeople and it's our own fault

It feels like every few years, the startup community figures out that they have a shortage. First it was engineers, then product people, then UX, and lately everyone has been coming to me asking if I know any good salespeople.

Now that might be the result of the rise in enterprise software but even SMB products are recognizing that they’re going to need a ground game and asking about how to build sales teams. And rightly so: whether it is through marketing or sales, in a world crowded with competition for our attention, even the best products need someone to bring them to market.

Here’s the problem: there aren’t enough salespeople to go around. And it is our fault.

Every shortage has had its unique contributors. There weren’t enough engineers because STEM education efforts hadn’t yet begun (and I’d argue this shortage continues because we failed to welcome women and minorities into engineering until very, very recently). We ran short on product people because it was a new discipline and nobody really knew where to find them or what to look for. Ditto for UX.

With salespeople, though, it is our culture that is at fault. And if we want to have enough to power the startups of the future, we have to make some fundamental changes in how we talk about sales and its experts.

Before I talk about culture, I want to dispel the myth of compensation as the cause. Certainly money matters. Because we have trained sales people to expect compensation that is at least somewhat commissioned based, the lifetime value of a product directly affects who you can get to sell it. If an advertising or finance sales gig can net you seven figures, startups tend to look less attractive.

But look at all the startup engineers. While it is mathematically true that the expected value of a career at a Fortune 1000 is higher than that of startups, they still leave big companies to go to startups in droves and plenty of new graduates end up there as well. The lure of being closer to the product, having more control, with greater connection to users and to the meaning inherent in the work captures plenty of attention. So clearly compensation isn’t everything.

Therein lies the much deeper issue. Borrowing Werner Vogel’s conception of startup folk as either missionaries or mercenaries, we have created a culture where we only allow salespeople to be mercenaries. “Salesperson” has become startup language for “necessary evil”. They are the lowest of the low, highly paid but never loved.

Even customer support gets more respect than sales. Fancily renamed into customer advocates, customer service is seen as the voice of users, feeding back into the great product cycle of launch and revise. They may be paid dramatically less than salespeople but they are given far more cultural credibility. Couple that with a low barrier to entry and rarely do you hear complaints that we can’t find enough customer advocates.
Cultural credibility matters. If the consistent message of startups is that they are the place you go for meaning, and we deny salespeople access to a meaning orientation, we are essentially denying them access to startups. So experienced salespeople don’t leave big companies and young people don’t go into sales roles.

I don’t blame them. If you can be a customer advocate, or a product manager, or really anything else, why would you pick a career where you will be consistently denigrated? Rather like young black men who opt out of continuing their educational journey because of the bleak prospects beyond, we can’t fault salespeople for acting rationally and refusing to enter into a world that constantly accuses them of being hired guns.

If we want to change this, we need to make a different set of cultural choices. We need founders to highlight and celebrate outstanding salespeople who helped them on the path to outsized exits. We need to start meeting salespeople where they are and genuinely wanting to learn more about their craft as part of broadening our own skillset. And product people and marketers need to actively solicit the expert opinion of salespeople and incorporate their feedback into design choices.

But most importantly, we must allow them to be missionaries. Just like any other startup role, salespeople have a particular skillset that they can choose to apply in a variety of ways. If we want to compete for their attention and convince them to choose to use that skillset on behalf of our products and services, we need to disentangle all our assumptions about motivation and personality from those skills. This isn’t Glengarry Glen Ross; nobody is getting murdered for sales leads. Good salespeople can help us save the world but is on us to invite them to do so.

Side note: If you are looking for salespeople, my best advice is to ask other salespeople if they know anyone who is looking. Homophily is still in play – birds of a feather really do flock together. And for my money, look at Mormons, psychology students, strippers, and anyone else who has looked public shaming in the face and made the shamers blink. Once you’ve had a thousand doors closed in your face when you started talking about God, or stood in a train station trying to get people to fill out surveys for hours, or counted on your ability to earn tips while naked to make ends meet, you don’t mind a little bit of cold calling and aren’t ashamed to make the ask.