95% of VPs of Sales Won’t Thrive at Your Startup - The Entrepreneurial Way with A.I.


Sunday, May 29, 2022

95% of VPs of Sales Won’t Thrive at Your Startup


So we’ve talked so much over the years on SaaStr on how to hire a great VP of Sales, the difference they’ll make, and how the level-up comes quickly.  And about when to know it isn’t working out.  And importantly, we talked about how there are 48 Types of VP of Sales — and you have to hire the right type to even have a shot at it working out:

But as I still see so many CEOs make a mis-hire in their first VP of Sales, I wanted to take just a minute to flip this all around and simplify it even further:

95% of the VP of Sales candidates out there that are “Pretty Good” — Aren’t a Good Fit For Your Startup

And in the end, this is the mistake so many CEOs make.  And VPs of Sales do, too.  It’s not that the candidate couldn’t be good somewhere.  It’s that it’s a mismatch.  And the mistake so many founders make is they want to believe a VP of Sales that’s good in general, good somewhere, would work at their startup.  Even when the signs are clear they won’t.

So a quick checklist here:

  • Don’t hire a VP of Sales that hasn’t worked at a start-up at least at the ARR you’ll be at in 12 months.  If you do, they just won’t know the playbook for your stage.  I don’t care how much the team likes them.  They just won’t know what to do at your stage.
  • Don’t hire a VP of Sales that isn’t truly comfortable selling to your buyer persona, especially in B2D and fintech.  A ton of great VPs of Sales have sold sales tools and similar products.  They know them.  They know the buyer, the use case, etc.  Especially in sales tools, because they live them every day.  But can they sell a search API?  A banking solution?  Often not.  I’d say roughly 50% of strong VPs of Sales that know the B2B playbook aren’t really comfortable selling B2D or fintech SaaS.  Be careful.
  • Don’t hire a VP of Sales that has no one good to bring with them.  It’s just a sign.
  • Don’t hire a VP of Sales that can’t demo your product.  Maybe later, much later, that can work.  But certainly not before $20m-$30m ARR.  And a lot of VPs of Sales won’t be able to do this if your product isn’t pretty close to what they are used to.  Hiring a bunch of SEs isn’t the answer here.  You may need them, but your VP of Sales has to live and breathe your product.
  • Don’t hire a VP of Sales that has truly done it all before.  Why would they join you?  If you don’t understand the motivation, don’t make the hire.
  • Don’t hire a VP of Sales that has never done outbound, if that’s important to your model.  A lot of VPs of Sales from companies with brands or PLG models aren’t used to doing real outbound.  You don’t have time for them to learn on your nickel.  You just don’t have the time.

Just remember, don’t lean in on a VP of Sales (or Marketing, the analysis is similar) that folks like, but just doesn’t have the background you need.

That’s 95% of them.  Just remember then, when your gut tells you the candidate won’t quite work, but everything else sort of checks out.

Push on.

And a few other classic related posts:


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Jason Lemkin, Khareem Sudlow