Once I take a look at the VP of Gross sales / CRO that didn’t work out the previous 12-18 months throughout the SaaStr Fund portfolio and my ecosystem, one factor stands out. And it’s an previous SaaStr theme:
👉 #1: You need to rent people in gross sales the place their final job was more durable.
There might exceptions at rocketships. When market pull is extremely sturdy and your model is #1, simply hiring skilled people could also be sufficient.
However 95 occasions out of 100, I see people in gross sales fail after they be a part of one thing more durable:
– When the product is extra sophisticated
– When the house is extra aggressive
– After they get much less deal assist
– When the product is extra technical
– When the customer is radically totally different
– When it takes 3-4 stakeholders to shut a deal, not simply 1
An previous SaaStr theme, however one I feel much more true right this moment, after we rent much more on logos, with fewer reference calls, and when extra veterans can be found.
It’s simply arduous to fly in gross sales promoting one thing a lot more durable to promote than your final position.
However promote one thing even a smidge simpler to promote than the final one?
You usually fly.
Even when it’s nonetheless actually needed to promote. As long as it’s only a smidge simpler to promote than the final one.
👉 Okay and the #2 motive seasoned gross sales execs (and others) fail: They Simply Aren’t Curious Anymore
I get it. What number of occasions are you able to promote considerably — sorry however — boring SaaS merchandise? Payroll? Insurance coverage? Voice APIs? Name middle analytics? Safety compliance?
They can be fascinating — however provided that you actually curious. When you aren’t, you by no means be taught something new. And that’s makes promoting something remotely sophisticated simply too arduous. You’ll by no means be an knowledgeable. You’ll by no means know how you can compete and win. And also you’ll simply run a primary playbook again and again.
Gross sales execs particularly that aren’t curious I see fail in any remotely aggressive house. Particularly on the VP degree and above. There is no such thing as a one to teach them, except they will get SEs and others to do many of the heavy lifting. And so they simply begin … making issues up. Fairly than actually studying.
In the event that they don’t ask good, curious questions through the interview course of — I say cross for that motive alone.
“The #1 motive I see VPs and executives fail right this moment — they by no means actually be taught the product. For actual. Chilly.” pic.twitter.com/1TSGIUwLRA
— Jason ✨👾SaaStr 2025 is Could 13-15✨ Lemkin (@jasonlk) February 1, 2025
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And a associated submit right here:
(picture from here)