There’s an interesting corollary to the fact that the best SaaS companies grow faster than ever today.

The corollary is that the window to hire a Stretch VP is shorter than ever.

  • If you hit $1m ARR growing 6-8% a month, you can probably hire a Stretch VP of Sales any time the following 12 months.
  • If you hit $1m ARR growing 15-20% a month, you probably only have a 3-6 month window to hire a Stretch VP of Sales.  Before you outgrow her too quickly.

We’ve talked a lot about Stretch VP hires on SaaStr, and Brendon Cassidy did a great dedicated piece here recently.

The reality is when you go to hire your VPs, you’ll be left with 4 types:  1) Stretch, 2) Absolutely Perfect, 3) Too “Heavy” — (i.e., needs too much infrastructure to scale at your stage), 4) Nice LinkedIn / Resume — But Not Actually Good Enough.  And maybe 5) a search for a unicorn that does not exist.

So Stretch is what many of us go for, and should go for, unless you just raised a $50m+ Series A.  Yes, if you’re a Second Timer and just raised $50m in your Series A, you can afford 3), the “heavy” VP hire that needs a staff of 6, or 25 AEs, to get going.  But most of us can’t.

OK so what’s the simple point?

Here’s all I’m saying:

  • A Stretch VP is a stretch.  So she’s gonna need 3-6 months not just to hit her number (which she’ll probably do), but figure all the rest out.  Really, how to scale the team.   Because it’s truly building a team that is the biggest stretch for most Stretch VPs.
  • So … plan where your ARR will be in 6 months and make sure she’s the right VP hire for then, too.  Not just for now.  This is the mistake I see all the time.  Someone you could have hired at $1m ARR, and grew into the job over the coming months as you grow to $3m, $4m ARR … instead, you hire at $4m ARR … and it’s just too late.


  • Once you cross $4m ARR or so — it’s often a bit too “late” for a true Stretch VP.  You now have to hire someone that’s taken a team from $10m to tens of millions in ARR at least.  This is the big mistake so many CEOs make when they wait too long to hire a VP of Sales, and outgrow the window of a true stretch hire for the role.

So as your ARR builds from $500k to $1m, to $3m and $5m … that “Stretch” VP has to stretch just so much further.  And you probably have to hire the VP that’s really done it before, at least, up to a point 3-5x bigger than where you are today.

(note: an updated SaaStr classic post)

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