Dear SaaStr: My Top Sales Rep Made $600,000 a Year — And Just Quit! What Happened?

Ok to some of you this will make no sense.  But now I’ve seen this happen again and again, including just the other day at one of my top portfolio companies.

The #1 or #2 rep in a start-up, that’s making lots of money, and has it all dialed in, and doesn’t want to be a VP or Director — still quits.  Often, for another job where realistically, they won’t make nearly as much money.  And often, where the working environment isn’t clearly any better.  And where they have to start all over again.

Why would a sales rep quit a job where they are making top 1%-5% money, respected, treated well, and have it dialed it?

It may not be 100% logical, but looking back, here’s where I see it happen:

  • A new VP of Sales comes in.  Always a risky time.  The #1 rep will usually stick it out, but if they don’t feel they are treated well, they may leave.  Even if they are treated well — just not the same as before.  The best VPs of Sales know how to handle this.  But hire a mediocre VP of Sales?  You’ll often see the #1 rep leave for the hills pretty shortly thereafter.  A real risk.
  • The VP of Sales leaves.  Also a risky time.  Often, the #1 rep is sheltered and protected by the VP of Sales.  Anxiety levels can go up if their VP leaves.
  • Their comp goes down, or simply, looks harder to achieve.  A sales exec I know in their first true AE role was the #1 rep at a startup doing $20m ARR, and made almost $800k.  She quit to go to a big public company as one of hundreds of reps, and start over.  I asked her why.  She said the next year just looked a lot harder.  But so it was for almost everyone.

The constant here?  Change.  We all think folks understand there is change in startups, and they do.  But often the #1 rep doesn’t want too much change.

After all, it’s the current environment, not some new one, where they’ve thrived.

There’s a bit of a theme here, which is that you can’t 100% control this.  Your #1 rep leaving when there is — change.  But here’s what you can do:

  • Make 100% sure your new VP of Sales and #1 rep are aligned.  Yes, it’s the VP of Sales’ job, but often it’s an odd dynamic, when a VP of Sales comes in and realistically doesn’t know the product, customers, and motion nearly as well as their new top report.
  • Involve the top AE in the recruiting process for the VP of Sales.  I actually haven’t found this makes a ton of difference — but still, do it.  It shows respect.  It’s how you’d want to be treated.
  • Give them space.  Spending even more time with your #1 rep in times of change doesn’t seem to help.  A lot of CEOs want to do this, they love selling with their top rep.  But it doesn’t help.
  • Don’t ask your top AE to do more than … be the top AE.  Sometimes as founders, we lean on our top individual contributors too much, even inadvertently.  We want our top engineer to also be a team lead.  Our top SDR to help manage the other SDRs.  Our top AE to help guide the rest of the team.  But individual contributors often only want to do just a little of this.  Ask more, and you can breed resentment.  I’ve made this mistake several times myself.  The best ICs (Individual Contributors) often just want to be that — and nothing more.  Don’t force them to do more, even a bit more, than they want to here.
  • Let them know they can come back.  Sometimes, this is really the best you can do.  We’re all on our own journey.  A bit more on that here.  They often see later it was a mistake to leave an environment that was perfectly suited for them.  Make sure they at least know their desk is still waiting for them.  You’ll still want them and need them 12 months from now, too.
  • Finally, a truly great VP of Sales will solve this problem for you.  They’ll know it’s their job to make sure the company isn’t overly reliant on one rep.  But also to keep their top performers, period.  Mediocre VPs of Sales keep their low performers.  But Top VPs of Sales make sure the top AEs stay when they join.

Change.  It’s the one constant in startups.  And oddly, and counterintuitively, it may lead your #1 rep to leave.  For something objectively … worse.

A related post here:

Is Being a Top Sales Rep … Better Than Being a VP of Sales?

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