I recently participated in a panel discussion about go-to-market strategies as a company moves from startup to scale up. I found myself at one moment challenged by the moderator when I asserted that the founders have to do the initial sales.
"Wait a minute," he said. "I suck at sales. I shouldn't hire a sales person to go out and pitch my product."
I pushed back pretty hard. "No, you shouldn't." My point was this. If you, as a founder, don't have enough intellectual curiosity about your customers and the type of problems you're solving for them, then you'll have a difficult time getting the sales effort off the ground. You need to get out of the building and go find your initial set of customers. That is the primary way that you'll learn about what really hooks customers and why they buy.
With that understanding, you'll have set yourself up for a more scalable sales operation. You'll need to do the initial sales training as you bring on your first sales people. Your training and coaching needs to come from your own experience to be credible.
I've been in two startups where we hired sales people prematurely to sell the product without the founders or at least the executive team making enough first sales to learn how it works -- who is the buyer, how much are they willing to pay, what is the real value proposition. We couldn't get traction because we didn't fully understand these things, and a bunch of hired guns isn't going to replace that hard work.