Spoiler: You can’t hire out sales because in the early days it’s about learning, not selling, and hired guns can’t bring back bad news.
At their peak, Groupon sales reps made 1250 calls per week to close 4 sales. Once Groupon knew the math of that equation, they could throw money at the problem and scale a sales team. Until you have the roadmap nailed down, you can’t scale sales (it would be like throwing money at a big search campaign before you know your lifetime values and conversion rate).
Your sales roadmap is a asset built up over time which undergoes the same innovation & refinement of a tech product. It takes time to get the roadmap solid. It’s as big of a deal as getting your viral loop working — it’s how you’re going to acquire customers at scale.
As a tech founder doing sales, you’ll find yourself constantly fantasising about hiring in a sales guy to take all your pain away.
The problem is, early stage sales isn’t about making money. It’s about finding out what people care about and figuring out what the sales roadmap looks like.
When you’re figuring this stuff out, there’s going to be bad news. Lots. And when hired guns bring back bad news, they either get fired or ignored. It’s the same reason you can’t outsource customer development. The bad news needs to be discovered by the founding team in order for it to be integrated strategically.
The founders have to do the early sales. Get help from wherever you can, but make sure to be in the meetings yourself. The goal is to discover and refine a repeatable sales roadmap. As soon as you’ve got that, you can hire it out. But while you’re still learning what works, it’s all you.
 Probably not true in all locations and not sure it’s up to date. This is based on conversations I had with Groupon folks in the London office over a year ago when they were at the height of scale fever.
 The roadmap is your funnel — the series of steps a prospect goes through before converting. Your pipeline is the leads who are currently within the funnel.
 The three workarounds are (1) to suffer through it, (2) to add sales guys to your founding team, or (3) to choose an idea which doesn’t rely on sales.