The #1 and #2 Reasons I See Sales Execs Fail Today

When I look at the VP of Sales / CRO that didn’t work out the past 12-18 months across the SaaStr Fund portfolio and my ecosystem, one thing stands out. And it’s an old SaaStr theme:

👉 #1: You have to hire folks in sales where their last job was harder.

There may exceptions at rocketships. When market pull is incredibly strong and your brand is #1, just hiring experienced folks may be enough.

But 95 times out of 100, I see folks in sales fail when they join something harder:

– When the product is more complicated
– When the space is more competitive
– When they get less deal help
– When the product is more technical
– When the buyer is radically different
– When it takes 3-4 stakeholders to close a deal, not just 1

An old SaaStr theme, but one I think even more true today, when we hire even more on logos, with fewer reference calls, and when more veterans are available.

It’s just hard to fly in sales selling something much harder to sell than your last role.

But sell something even a smidge easier to sell than the last one?

You often fly.

Even if it’s still really had to sell. So long as it’s just a smidge easier to sell than the last one.

👉 Ok and the #2 reason seasoned sales execs (and others) fail:  They Just Aren’t Curious Anymore

I get it.  How many times can you sell somewhat — sorry but — boring SaaS products?  Payroll?  Insurance?  Voice APIs?  Call center analytics?  Security compliance?

They can be interesting — but only if you truly curious.  If you aren’t, you never learn anything new.  And that’s makes selling anything remotely complicated just too hard.  You’ll never be an expert. You’ll never know how to compete and win.  And you’ll just run a basic playbook over and over.

Sales execs especially that aren’t curious I see fail in any remotely competitive space.  Especially at the VP level and above.  There is no one to coach them, unless they can get SEs and others to do most of the heavy lifting.  And they just start … making things up.  Rather than truly learning.

If they don’t ask good, curious questions during the interview process — I say pass for that reason alone.

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And a related post here:

(image from here)