A friend of mine recently told me I was wrong and that I should have applied the Rule of Three. Why should you staff three people on a new sales project?
This friend, who has built a company of 500+ sellers generating $100M+ in revenue (and has also launched and sold two other startups), clearly knows his stuff. His concept of the Rule of Three is pretty simple but profound (like all great tips are):
Three sellers avoids "groupthink" and let's you best test a new initiative.
What do we mean by this? Well, two folks working together, in my friend's experience, often leads one strong willed person to influence the other more malleable seller. Two people end up operating much more like one, limiting true comparative testing.
When you have three sellers, ideally with very different backgrounds and experiences, it's harder for groupthink to develop. If two people go down a path that doesn't seem to make sense, the third will often push back and take a different approach.
So, while two sellers are better than one to test a market, I'd encourage you to apply the Rule of Three whenever you can to new sales initiatives. Of course, startups often have limited budgets and need to sell with the CEO and any/all other hands before hiring a first seller to begin. Accordingly, this model isn't always possible in all situations. But if you can afford it, I'd say go for it!