Every great hire starts before their first day
And often even during the interview process
— Jason ✨👾SaaStr 2025 is May 13-15✨ Lemkin (@jasonlk) January 12, 2025
#1. The Best VPs Start Before They Start
The best sales leaders start reaching out to a few great customers they already know. The best marketers are already building out a spreadsheet to increase pipeline — and show it to you for feedback. The best VPs of CS are already asking which customers they can fly out to and meet their first week, and already working on upgrading your CS systems.
If you aren’t sure about a hire — see if they start .. starting.
#2. The Best VPs Have Someone Ready to Join Them
Junior hires often don’t. But the best VPs not only know a few great folks in the industry — they want to bring them over with them. Always.
If they don’t have anyone to bring with them — they may still be good. But they aren’t a VP.
You'll know if your VP of Sales is going to work out even before they start
How?
You'll know based on who wants to already come with them pic.twitter.com/85ajodCHGK
— Jason ✨👾SaaStr 2025 is May 13-15✨ Lemkin (@jasonlk) October 14, 2022
#3. The Best VPs Have True Urgency
They push the interview along. They take the first time slot open. They want to get going — now.
Different folks express this differently. But if there’s no urgency at all during the interview — there won’t be any when they start, either.
#4. The Best VPs Are At Least Somewhat Flexible
They push you to be CRO, but you need a VP of Sales? They may push you on comp or timing or exact role. But in the end, they don’t make it all about the role, title, comp, etc. In the end, they know it’s a joint mission, and they are at least somewhat flexible.
If it’s my way or the highway, it’s OK to get pushed at first. But there is zero flexibility — push on.
#5. The Best VPs Are Truly Curious
And because of this, they ask good questions during interviews. And push you sometimes in areas you weren’t expecting to go into. And expect more transparency on the company. To be a great leader at a start-up, you have to have a curious mind. Because you have to grow, and grow quickly. The best VPs keep asking more and more good questions the more you interview them.
Not end the interview early — with no questions.
Struggling on whether or not to hire that VP? Ask yourself honestly if they passed the above 5 part test .. or not.
If they didn’t, move on. It’s better to struggle without, 9 times out of 10.
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