Over the years at SaaStr, we’ve done a lot of posts (and videos and sessions) on hiring your first great sales team.  I recently re-read a bunch using our excellent Algolia-powered search and wanted to share some of my favorites, updated:

1. Your First VP Does Not Have To Be a VP of Sales.  Looking back, this is just so important, I wish I’d written this in the earliest days of SaaStr.  Yes, you know you want a VP of Sales.  We all need one, almost all of us, at least.  But don’t let that stop you from hiring any other great VP first.  They are all accretive.  They all add to sales.  Read it here.

2.  10 Crystal Clear Signs Your VP of Sales Just Isn’t Going to Work Out.  Please read this one if you aren’t sure if your VPS is cutting it.  VPs of Sales get blamed way, way too often for things outside of their control. And fired and/or topped when they shouldn’t be.  But CEOs often stick with a failing VP of Sales way, way too long.  How to tell the difference here.

3.  What Core Metric Should Your VP of Sales Be Responsible For?  A very simple post, but a very important one.  You get what you incent.  Should your VPS be responsible for bookings?  Or ARR at year-end?  New business?  New business + renewals?  She or he will build a very different team, and work to very different goals, depending on what you pick.  Read it here.

4.  Yes, Your VP of Sales Also Has to Be a Great Salesperson Herself.  I highlight this one because I see this mistake made so, so many times.  A CEO loves a VPS that is smart, knows the terms, seems to “get it”.  But has never really been a killer salesperson herself.  Or a VP of Sales that really, really knows process, and builds great process slides.  But doesn’t really want to sell themselves, not really. This can work at Microsoft or SAP.  It will fail at your startup.  More here.

5.  How to Succeed as a First-Time VP of Sales.  Or VP of Anything, Really.  This guide was meant for stretch VPs taking the ring for the first time, but it also serves as a great reverse checklist for CEOs on where to push, and where not to.  If you are looking at being a VP of Sales for the first time, please read this post.  I see so, so many stretch VP of Sales get fired / quit in less than 6 months.  It doesn’t have to happen to you.  How to avoid it here.

6.  That Super Successful VP of Sales.  Great?  Or Just Lucky?  When you go to hire your VP of Sales, you’ll get excited by logos.  Be careful.  Because if you don’t dig deep, you’ll likely find someone more lucky than great.  Sales is tough, no doubt.  But it is just different when success has many fathers and mothers and parents.  More on the difference, and how to avoid this oh, so common, and avoidable, mistake here.

7.  If Your VP of Sales Isn’t Going to Work Out — You’ll Know in 30 Days.  Another super important lesson.  When I first wrote this, so many VPs of Sales hated the post.  But later, they all admitted I was right.  At least all the good ones did.  You’ll know if your VP of Sales is going to make it in 1 sales cycle at least.  Even in 30 days, if you pay close attention.  More on how and why here.

8.  How My VP of Sales Doubled Our Sales in 90 Days.  And No, It Wasn’t Magic.  Boy, this classic holds up.  How does a VP of Sales come off the street, with the same crummy leads as last quarter, and magically grow sales?  It ain’t magic.  It’s people, process, and team.  How it really happens, here.

9.  Six Key Signs Your VP of Sales Can’t Scale Beyond $5m-$10m ARR.  Even if your VP of Sales is working out, you have to be honest and ask if she can scale to the next level.  More often than not, she can scale further than you think. Don’t assume she can’t.  But there are some very clear signs she/he can’t grow further.  The top 6 here.

10.  Twelve of The Most Common Mistakes Made Building Your First Salesteam.  You are going to make a lot of these mistakes.  Just make fewer (and it’s not that hard) — and you will sell more.  I guarantee.  A great checklist here.

Want Even More?  The SaaStr team put together an incredible eBook with all this and more.  Download it here:


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