Startups should try to hire salespeople in pairs. This is particularly important when spinning up a new channel (e.g., launching in a new market, opening up a partner channel, or kicking off outbound sales). Hiring in pairs is helpful for a number of reasons:
First, knowing if a new sales recruit will succeed is difficult. Even salespeople with fantastic experience are unsuited to sell certain products in certain markets. Hiring the wrong person can be a serious setback when it takes a month to find out if they can do it, a month to recruit a replacement, and another month to find out if your second hire will make it. If you hire two people, you have a greater chance of landing at least one effective salesperson.
Second, when trying something new, like launching in a new market, opening up a partner channel, or kicking off outbound sales, it’s hard to know what your salespeople should achieve because there are factors outside of their capability that impact sales results. Suppose you hire one person to launch your product in a new geography, and they fail to deliver results that match your success in your initial geography. Many leaders will blame and replace the salesperson, only to fail again because the problem wasn’t the salesperson. In these situations, problems with the product, economic or cultural differences between your old and new markets, pricing, or other variables could cause poor traction in a new geography. When you hire two people, you can compare their results and, therefore, more clearly see whether traction challenges are people-related or otherwise.
Third, competition fuels sales performance. Salespeople notice when their peers book more meetings, close more deals, and earn more money than them. A lone salesperson is almost always less motivated than one with a competitive peer.
Most managers in early-stage startups think that chaos is inversely correlated with results. That is, they think that chaos breeds bad results and an unhealthy environment, while order breeds good results and a more harmonious environment. This perception is wrong.
The best salespeople have great intuitions for which prospects are most decisive, and how to get access to better contacts. Everyone else wastes their time talking to people who will never buy, no matter how appealing they make it sound.
To win, startups need to lean into their advantages because they’re a decade away from the kinds of moats enjoyed by established corporations. This means they need to work smart (i.e., mostly do the right things) and work hard (i.e., execute at a pace and with intense risk tolerance).
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