Sales strategy has to evolve over the life of the startup. Early on, you may have an experimental product, an experimental revenue model and theories you're working with. You may have some capital, either from friends-and-family or small VC investments, and perhaps a few advisors. But you're still probing to find found your target market. At this stage, typically no one knows the product and its potential market like the founder. And no one can sell the product as effectively as the founder.
One of the mistakes that entrepreneurs make is trying to set up the traditional structure for larger companies that is taught in business school. You put someone in charge of sales, someone in charge of marketing, someone in charge of technology, someone in charge of HR. But the company isn't yet a company. It's still an experiment hoping to become a company; until you have significant revenue, you're not a company.
So you have to think differently. You have to think entrepreneurially. When you're hiring your first key hires, you may hire somebody who in a former job was a superstar VP of sales, with similar domain knowledge. But what you're expecting that person to be is a founder. You're expecting him or her to be somebody who is not rigidly into the sales process, who is entrepreneurial and can work with you on all aspects of the business. What you're ideally looking for is an alter ego.
Suppose you're an entrepreneur with limited capital and you know you need to make a key hire to advance your business. Your first excuse is, "I don't have enough money." You want to hire someone great, but you end up hiring someone mediocre because he or she is available and willing to work at a price you can afford. That's not a good recipe for success. Hire someone mediocre and you can expect mediocre performance. Ultimately, that person will require a lot of training downstream; too often, you realize after a couple of years that you simply need to replace that person.
To hire a superstar, you have to take a different approach. Can you identify the absolute all-stars in the market for the position your trying to fill? Most founders can't, and most don't do enough work trying to identify who they are. Some people hire search firms, and some search firms do a fine job. But seldom do they do as good a job as a founder who is willing to put in the time and effort. VCs and board members or advisers can help, but ultimately it comes down to the founder following a very disciplined sales process.
If you want to hire an all-star VP of marketing, start by identifying the 20 greatest marketing stars in your business area. You may look at that list and think, "There's no way I can get any of these people. They make a salary five times as much as I can pay. They're already too successful to work at my startup." But that's not the point. The point is to start with the very best and do everything entrepreneurial in your power to get to these people. Then, essentially flatter them and say, “I know you'd never come work for me, but you are the top of my all-star list and I just really have to buy you lunch.” Talk to them about the job and try to sell them on why they should forgo everything they have and join your little startup. Several outcomes are possible: