So there’s a sort of org chart you’ll probably end up with at least twice as you start scaling in SaaS:  The “Headless” Sales Org.

What’s that?  It’s a bunch of sales reps without anyone to manage them other than … you.

There are basically two times I see this happening, and it happens to most of us:

First, when you are just getting going, and doing founder-led sales, you start off “Headless”

Your job as founders is to close the first 10, 20, 50 customers yourself, then bring on a few reps, then get those reps closing, and then … hire a VP of Sales to scale it from there.

But if you end up not hiring a VP of Sales at that perfect moment in time (and most don’t), you’ll end up headless.  With 3, 4, 6, 10 sales reps all reporting to you.

This doesn’t fail, per se.  The Headless Sales Org rarely fails per se, and that’s the important part.  It just underperforms over time, often by 50% or more.

There is no way as you are just finally scaling as CEO that you have time to also manage 8 sales reps.  So they end up self-managing, and often what you see is the top reps still performing well.  In fact, they often keep a lot of the best leads for themselves, since you don’t have a true VP managing things.  But everything sort of gums up, and you have trouble bringing on more strong performers.

Second, most of us end up with a “Headless” Sales Org for a little while if we move on from our first VP of Sales.

If you’re lucky, if your first VP of Sales doesn’t work out, someone under them magically rises to the top as your new Head of Sales.  This doesn’t happen most of the time in my experience, but it does happen frequently.  A Director of Sales that is successfully managing 3-4 reps and can hire, steps up and takes their shot.  If they can hire, I say give them their shot.  Because they’re known, proven, and generally trustworthy.  Back those that raise their hand.  Generally, that’s less risky than bringing in an outside, if you truly believe they can do it.

But in many cases, no one raises their hand, or that resource doesn’t exist.  So you fall back into a structure a bit like the early days, with 3-10 reps all reporting to you.

At first, it actually can feel better, especially if there was tension with the old VP of Sales. In fact, your top 1 or 2 reps generally prefer this “Headless” environment.  This is a super important dynamic to understand.  They will push back against bring in any new VP of Sales that isn’t clearly accretive to them.  Your top performers will quietly encourage the Headless environment, at least at some level.

But again, everything degrades:

  • Without a VP of Sales, there is no one to own the overall number.  Individual reps may still do well, but with no one sweating the overall ARR growth number, growth always suffers.  Always.
  • Without a VP of Sales, recruiting stalls.  No one owns it.
  • Without a VP of Sales, it’s very hard to manage SDRs.  It’s a lot of work managing an outbound team.  AEs can’t do it and/or don’t want to do it, not really.

I’ve seen the Headless Sales Org in almost every startup I’ve invested in, and I’ve been through it twice myself.  And what I can tell you is — you sell about 50% less.

It’s OK for a little while.  Don’t make a mishire in your next VP of Sales.  That’s far worse than a Headless Sales Org.  And a month or two or even three as a “Headless” Org can be mostly fine.

But after that, it degrades. Trust me.  Try to not have a Headless Sales Org last longer than about 90 days.

(no boss image from here)

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