Does this situation sound familiar? Your product is about to go into beta. Your employees are all engineers or product people or designers. You, the CEO, are the lone business person. You know that you have to figure out monetization (you've been telling people your model will be "freemium" but you haven't really done any work on nailing down the details). You're not sure what your pricing structure should be. You might have a pre-beta list of email addresses you've collected from a sign-up page you drove people to. But, there are lots of things you don't know and need to know:
-- What's the profile of a typical customer and how do I source and qualify them?
-- Who to sell to (product manager? head of marketing? head of sales?)
-- What to charge and what pricing tiers to offer?
-- How long does it take to make a sale and what's the ratio of leads/sales?
Basically, you don't know squat about selling your product and what it's really worth to the market.
The natural inclination is to hire a salesperson to "figure this out." But this is where a critical mistake is often made, and I want to talk about a generalization I like to make about sales people when making hiring decisions.
I believe that there are two kinds of salespeople: Expeditionary Salespeople and Process-Oriented Salespeople. (In general, I'm skeptical of people who divide the world into two buckets, so I understand any skepticism that comes from my doing just that.)
They are both extremely valuable. But, they are valuable at very different times in your company's life cycle. Hire one type at the wrong time and you're almost certainly going to part ways or radically undershoot your potential.
Expeditionary sales folks are fantastic in early, ambiguous situations. They don't mind selling an incomplete product. They relish in calling nearly anyone that they think might have a need for what you've built and in learning about product/market fit. The great ones don't just report back to engineering "the customer wants X, please build," but instead use judgment and knowledge about what you've already built to map to what the customer is trying to do (but not necessarily asking for). They can make up pricing on the fly if necessary. In short, they almost look a bit like business development folks, but the key difference is that they thrive on the game of getting people to open their wallet and spend.
Let me give you an example. At JotSpot, our first sales guy was a guy named Eugene Levitsky. I hired Eugene right about the time we were going beta. We had 15,000 email addresses of people who were interested in getting access to our service when it was ready. We suspected we were going to be a freemium offering, but we had no pricing structure in place. We had let perhaps 100 people use what we had built.
Eugene dove right in. He called on our first 100 users. He sussed out what they were using it for. He sensed when it was being used for something critical and started asking people for money (despite the product being in beta and us having no published pricing). He tested lots of different prices on the fly. He tried various pitches to convince people that what we were doing was valuable. In short, he made a ton of things up, he explored a huge range of prices and pitches, and he zeroed in on what worked. In the sales world, he was doing the equivalent of the rapid prototyping that great product organizations do. He was perfect for that stage of our business.
So, what are expeditionary sales guys bad at? Well, in general, they like new challenges. When something feels figured out, they get bored. They have greater resistance to traditional sales quotas and targets (but they know they come with the territory). They certainly don't like formal processes because they feel "too rigid." And, for the most part, they're not thinking of how to build a massive sales "machine" with repeatable methods for identifying and qualifying customers, checklist-driven processes for engaging with customers, and banging the phones or email queues to drive sales.