So much of classic SaaStr content is on getting that first VP of Sales hire right.  Getting it wrong so often sets you back a year, and burns half your cash.

But the reality is many of you will hire a Pretty Good First VP of Sales.  Just not a truly, truly great one.  And that can be fine either for a while, or if they grow into a great one, forever.

And then I see the same mistake again, and again, and again.  A founder hires a Pretty Good First VP of Sales.  And just … exits sales.

They didn’t love doing founder-led sales.  Or they want to get back to doing product.  Or they think they are sort of done with this.

I can tell you almost 100% of the time, any but the very, very best first VPs of Sales fail if the founder steps out of sales.


  • They need time to learn the product:  The CEO can backfill here.  The CEO in the early days is often the best demo’er, best tough question answerer, and the best sales engineer on planet earth.
  • They need time to learn what really works: The CEO knows.  She’s closed the first 50 customers herself, or with the first few AEs, after all.
  • The customers and prospects love, love, love to talk to the CEO.  Forever.  This is a huge boost the sales team loses if the founder exits sales.
  • Until you have a brand, the CEO is a lot of what customers are investing in.  If the CEO exits sales, there is less for prospects and customers to invest in.
  • The VP of Sales never gets their feet under them.  They never have a shot to build confidence when the CEO exits sales.  And you need confidence to win in sales.
  • They need to learn what type of AE and SDR can work at your startup: The CEO doesn’t always know who to hire in sales, but they do know what doesn’t work.  Being deeply involved in hiring really helps here.

So again and again, I see a Pretty Good VP of Sales hired at $1m, $2m, $3m, $4m ARR.  And the CEO is off to the next thing.  And sales — decline.  They don’t even flatten, they decline.  Because you’ve lost your best asset on the sales team.  Sometimes, if you hire a VP of Sales that was already a customer / user, they already know a lot.  And the very, very best do figure it out.  But otherwise, it’s the Titanic if the founder exits sales.

As CEO, assume you never get that time back just because you hired a VP of Sales.  You always have to put the same amount of time into sales.  No matter how great a VP of Sales you hire.  It’s just, what you do with your time in sales should change.

You shouldn’t have to send contracts out, or do routine follow-up.  The VP of Sales will make sure that all happens.  But you still have to put as much time into sales.  Just in more valuable parts of the process.  In the middle of sales, and just in bigger deals, and smoothing over issues.  And building relationships.  But not stepping out, or putting in less time overall.

Exit sales, and watch sales fall.  I can almost guarantee it, unless you truly hire the best of the best.  And most of us don’t.

A related post here:

The 2 Things To Look For — At a Minimum — In Any First VP of Sales. And 3 Flags Almost Everyone Misses.

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