Knowing when to hire your first sales person is the answer to one of those million dollar questions. We did a great job hiring our first sales person at Gnip (an Enterprise SaaS sales scenario), and this post describes how I think we pulled it off.
There were three things I wanted us to have before we pulled the trigger.
I wanted us to have some actual revenue first. Not a ton, but a handful of months that showed growth. Something I could show a salesperson prospect and say, "See, there's growth here. Your job isn't to start the growth, it's to increase the slope of the curve!" Of course, I also wanted some revenue and growth trajectory to convince ourselves that we were onto something too.
I wanted us to have some semblance of a pattern that illustrated the deal process and showed a prospect coming into the top of the sales funnel, and then out of the bottom, cutting us checks. This pattern, or template, would be something we could hand to a salesperson prospect and say, "This is how we've gotten this far. Are you comfortable with a model like this? Can you make improvements to it so we can have more money flow in?"
I wanted us to have the experience of having done the first wave of sales in order to really know what we were up against.
Put all that together and I think what is was, was that I wanted the upper hand in bringing on our first salesperson. Without the above, you're at the whim of the salesperson, because.... well... "You don't have a proven model here." Danger, danger.
I did NOT want us passing the sales buck off onto some new hire that couldn't fully understand our product, our prospects, our customers, our software, our challenges, our margins, etc. Understanding all of that stuff takes many months, and you want this person generating money quickly. I firmly believe hiring someone to sell your stuff before you've achieved the above items is a recipe for disaster. It will end with the firing of anyone you hire. You will fire them because "they don't understand our product" or "they don't understand how to sell our product" or "they don't understand our customers" or "they don't understand where they can flex on price." Those are all reasons you need to sort out before you hire your first salesperson. Now, you may have to let your first salesperson go anyway, but don't start off with one hand tied behind your back.
Oh, and another thing, I didn't want to hear the new salesperson say "you've never sold this product successfully. I'm trying to get our sales engine going here. it's going to take time." Fuck that. No excuses.
My board of directors drilled into me that we would fire our first salesperson hire (whoever they turned out to be), and that was something I was going to have to be prepared for. Our first salesperson drove Gnip into shit-tons of revenue; years later he's still with the company.
Your mileage will vary.