Answer by Jonathan Brill, Startup Specialist, on Quora

Most people have sold something to somebody at some point, and so may get the general feel of what it means to pitch. But my experience is that running sales at a startup, particularly one that still has to prove itself, is a unique experience that’s far less covered in the startup press but far more common than people realize. Here are some of the things unique to running sales in an eat-what-you-kill culture.

Making payroll is more important than making commission. At one particular startup I was employee number 7 and we had over 70 after about a year and a half. By all appearances, we were doing great. Our client list had blown up, we had a great pipeline, I had built the foundation of a smart, veteran sales team, and the future generally looked great. But despite having great investors and great prospects, there was no question that one single missed quarter could hurt our chances for raising another round of funding and we’d have to lay off most of our employees.

Every single time I walked through our engineering pit or ate lunch with the folks in quality or got coffee with the product managers, I was reminded that they were all depending on me for their livelihood. And more than that, they did this with blind faith. Whereas I had up-to-the-minute forecasting models and a lifetime’s worth of expert intuition about which way the pipeline would lean, they just had to take my word for it. There was never any commission or sales chart that would move me more than knowing an extra ounce of persistence or preparation might make the difference in whether these people whom I worked with would get paid on time. I sat next to them, I knew their kids and spouses, we talked about their future and their vision for the company, and every night I’d drive home thinking about making payroll.

Finished product is a nice to have. Upon taking a job to run sales at a VC-darling in the storage security space, I was asked to go visit our tier 1 beta customers and start getting some new ones. In preparation for the trip, I asked to see the product documentation. There was none, but it was being built. So I asked to sit with the tech writer who was building it. No problem, except that she was only building docs for what the product would eventually do, not what it did right then. Rather, the product I was given to go out and sell right then didn’t have a Graphical User Interface. Sure, they had big plans, but knocking on doors to sell an enterprise infrastructure app with only a Command Line Interface either seemed suicidal or silly.

After a string of odd meetings, we actually got some sales and parlayed that into a distribution deal with one of the largest storage companies in the world. Our product vision and comically improbable traction with a CLI gave us a ton of credibility and eventually led to an $80m acquisition. At no point did the company ever have a product that could be installed and used without constant tinkering from the company that made it.

Very often, the VP of Engineering, the CEO, and the Board of Directors will be waiting for you to tell them what to do. In a small company chasing big revenue sales, the last person to speak to the customer is the most important person in the room. And if you’re a couple years down the line and you’re the last person to speak with all ten customers, then everybody else’s board slides are a detail. In fact, I remember our board giving that feedback directly to my CEO – they told him to cool it with all the strategy slides and make more time for pipeline. This is very common in small companies because one giant deployment can sap 20-30% of the company’s resources for a year or more. Failure to close or failure to get the right kind of deal can set you back a full cycle.

The truth is that in these situations, it’s common for the head of sales to be the only one with the contacts and the experience to judge the likelihood of a close. There’s nothing wrong with this per se, but it’s awkward. I remember being in executive meetings with our VP of Engineering who had 30 years on me and he’s asking me what his priorities should be for the next quarter. This could be true in most of your meetings; it was certainly true in mine.

When I started out in sales, I really thought I’d be doing more Boiler Room, Glengarry Glenross-type calling. But sales, just like every other important role in a startup, is more about long-tail activities that help the company and customers get what they need than hitting some arbitrary goal.

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