A rough structure from 1–25 sales reps:

Early days:

  • CEO acts as VP of Sales.
  • CEO hires 2 reps, in the beginning, each barely pays for themselves, but by months 4–6 they are able to close 3x or more of their total compensation.
  • Once 2+ reps can do 3x-5x their comp, the model gets pretty efficient.
  • Sometimes, a CEO enjoys outbound (or at least is decent at it) and hires 1-2 or more SDRs themself and directly manages them.  But most founder CEOs don’t have the background or patience to do this.


  • Have to scale from reps 3–8 or so. CEO often struggles to manage so many directly, trains them poorly.
  • CEO starts looking for true VP of Sales by $1m ARR, ideally hires one by $1m-$2m in ARR.
  • VP of Sales hires next 5–10 reps herself.
  • If VP of Sales is good, most of reps 5-10 perform.  If VP of Sales is weak, these later reps all fail compared to the first 2 reps that hit quota that the CEO hired.
  • If the VP of Sales is good at outbound, they also start to build an SDR team here.  You really can’t start too early if you are good at outbound.  It almost always works — done right.

Outbound Always Works. If You Do It Right. And You Put In The Time.

After 8–10 reps, you have to add more management:

  • A VP of Sales can probably only manage 6–8 reps and a handful of SDRs directly themselves.
  • So for each 8 AEs or so, and 8–10 SDRs, you need a Director of Sales.  Big companies often call these “RVPs of Sales”.
  • You also start specializing more here. Segmenting by customer size, and sometimes geography.
  • By 8-10 sales reps, you probably need a first head of rev ops / sales operations to handle training, onboarding, compensation, quotas, etc.
  • If you are well funded, you can lean into rev ops earlier.  It almost always pays off even earlier, if you simply get your reps performing more efficiently.

This is a rough guide.  It can vary based on segment, and the skill set of the CEO and the first VP of Sales.  But if you see something radically different from this … you may be making the wrong hire.  Likely, someone that is either too late stage for you, or someone that hasn’t really done it before.

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