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

So the other day Collin Cadmus, who was VP of Sales at Aircall, summarized a career question I’ve thought about many times over the past 10+ years.  If you are a great AE, a great individual contributor sales exec … I know you might want “more” than that, more from your career … but is it really better to be a VP of Sales?

I’ve met with so many ambitious AEs over the years who wanted to make the jump straight to VP or “Head of” Sales.  I often counsel at least some patience.  Patience to yes, still make the jump.  But once you have at least the base skills.  And once you know it’s actually … better.

There’s a trap I’ve seen many times where especially first-time VPs of Sales skip too many steps.  Especially the ones that go straight from Top AE to a first-time VP of Sales.  Because if you really are the #1 rep at a hot SaaS startup, a founder will give you a shot.  They’ll get you the VP or “Head of” title just because you were the #1 or #2 rep at a top startup.  Even if you have zero management experience.  Even if you’ve never hired a single top performer yourself.  But should you take that job?  Should you skip the steps of first being a team lead, then a Director, then building a great team yourself (not just inheriting one) … before you go for VP of Sales?  I’d argue yes.  5-6 years is about the absolute fastest you can mint a Stretch VP of Sales.  I so often see first-time VPs of Sales fail simply for not having enough proven hiring and management experience under their belt.

Dear SaaStr: What Percentage of Software Sales Reps Have Earned Over $1m a Year?

And there’s a related point above.  If you really are one of the Top 5% sales reps in a fast-growing, successful startup, especially one of the Top 1-2 … you can potentially make just as much or even a lot more, with less stress, than as a VP.  Not zero stress.  But less stress.  The top reps at successful startups tend to get very, very good at running the playbook.  They often close 2x, 3x, even 9x more than the average rep.  And thus, at least in the right places, they can make a lot of money.  Without the bar to double or triple next year that hangs over the head of a VP of Sales.

I remember as I was building my first sales team, I heard the classic story of how the top blackjack dealers in Las Vegas often make more money than their managers.  They get promoted, then they deal the top tables, and the tips are so strong, they make more than their bosses.  And go home at the end of the day with, I presume, fewer worries.  I’m not sure if that’s 100% true everywhere today, but the point stayed with me.  Especially once I saw that the top AEs could really make more than their VP once a SaaS company starts to cross $10m ARR or so.  Not most AEs.  But the top ones.  The ones that really can close 5x-9x more than the rest.

VP of Sales is a tough job.  Every year, the number just goes way, way up.  For the right folks, it can be insanely rewarding.  You can build and spawn the careers of many leaders.  You get to be part of the leadership team, work directly with the founders and investors, and so much more.  And VPs of Sales are often the only ones in sales to get significant equity.  So if you want big equity, you’ve gotta get to VP.  But for cash?  For quality of life? For security?

Being the #1 or #2 sales rep can be just as good and, for many, really better than a VP of Sales.  At least for many top sales closers.  At least think about it before you rush to make the jump to VP of Sales.  At least, do it for the right reasons.

A related post here:

The Double-Stretch Hire Rarely Works Out

Published on January 19, 2023

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