Sales Leadership

Hiring a VP of Sales, Read to Lead, The Better You Get, The Less You Care

Happy Sunday!

Have you ever wondered what it takes to land a VP of Sales role?

What if you’re a founder and looking to bring on your first sales leader? How do you make sure you’re hiring the right person?

Jason Lemkin covers the 10 questions you should ask every candidate:

Great sales leaders know how to scale, but hire the wrong one, and you’ll lose a year.

The biggest mistake you can make in hiring salespeople is getting mesmerized by the logos on their resumes.

Don’t get starstruck just because they worked at Twilio, DataDog, or CrowdStrike. Their success may have been inevitable at these companies. Make sure they weren’t just riding a massive wave by asking the right questions.


The questions in the video above can help you:

  • Determine the knowledge you need to qualify for a sales leadership role.

  • De-risk your hiring process when bringing on your first sales leader.

Here’s is how Matt Marshall, CRO at Spiff, determines if his sales reps are ready for leadership:

You Must Read to Lead

A leader must be a reader. We must learn from the experiences of others. We must be challenged. We must exercise our brains. We must prepare ourselves for the things we’ll only be able to experience once, by learning from the experiences of others.”

I can’t wait to dive into Invent & Wander, a collection of writings and public statements by Jeff Bezos—the greatest Founder/CEO of all time. I noticed a lot of people hating on Amazon this year. People seem to forget that before Jeff Bezos became the richest man in the world, he was grinding it out (day and night) in a makeshift office. 

Instead of denigrating American entrepreneurs, we should stroll to the local bookstore and pay 30% to 50% more for our books. But, who wants to do that when you can get it delivered to your Kindle with a single click?

The Better You Get, The Less You Care

Speaking of people who are hated on, Eminem just dropped a new set of tracks on Friday.

One of the reasons I admire him is his unwavering dedication to his craft. The haters keep telling him to hang it up. He’s too old to be rapping. But, his lyricism continues to get better, and he doesn’t do it for the money.

This is a common trait among elite performers. Dave Chappelle said he doesn’t even care about the crowd anymore. His only concern is getting one step closer to perfecting his craft. He doesn’t try to appeal to the masses.

If you want to be great, let go of your desire for external validation. Pick your lane and aim to get one step further each day. If you tie your well-being to a dollar amount or a title, you’re putting your happiness in the hands of others.

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