Dear SaaStr: Should a Startup Founder Handle Sales Themself When First Getting Started?

The answer is yes – 95% of the time.

The “best” sequence for building a repeatable sales engine is roughly:

  • The CEO/founder should close at least the first 10 (or 20 or whatever) customers. That way, she knows. She knows the process, what works, what doesn’t. It’s OK if you are “terrible” at it. What matters is that somehow, someway, you still get those 10 >paying< customers closed.
  • Then, hire first 2 reps. Not just 1. To reproduce what CEO did, managed by CEO. If you only hire 1, you can’t run an A/B test and really learn what works at the rep level.
  • Ideally, hire your Head of Demand Gen around now. Even though you may not have that much revenue or that many leads, he will help you get more leads and maximize the experience of the leads you do have.
  • Then, once you have 2 reps that can hit quota (even a modest quota) — you are ready for a VP of Sales. Because her job isn’t to figure out how to sell your product. It’s to scale a tiny engine into something bigger. To hire reps 3–300. To go bigger, stronger, faster. But not to figure out if you really have a repeatable sales process.

This is the “best” process because it’s the fastest and most efficient.

But, sometimes a founder is >so< terrible at sales, so awful at it, that literally, it’s hopeless.

In that case, hire someone to do sales for you before you’ve even closed 10 customers yourself.

But it’s super risky.

How can you figure out who to hire, if you can’t even close 10 customers yourself? Really … you can’t.

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