How To Still Hire a Great VP of Sales Even If You Are Struggling

When you are finally ready to hire your VP of Sales, oftentimes, there’s often a bit of a quiet panic around time.  About getting the hire done.  Because there’s a window.   Even if you are growing like a weed up to $1m, $2m, $4m ARR, or beyond … you can see growth is going to slow down without help.  You can’t hire more reps yourself.  You don’t know the rest of the playbook and don’t have the rest of the toolkit.  You can see that even with great sales rep efficiency with, say, 1-3 reps, it is going to slow down unless you bring in that VP in time.

And indeed, it often does.  If you don’t hire the management you need for each stage, you’ll almost always at least slow down at each phase transition.

But then, so often, I see startups still able to hire a great VP of Sales even after sales slow down a bit.  Often, to much less than outlier rates.

How?  Why?  Why would a great VP of Sales join a start-up with mediocre growth?

Because great VPs of Sales aren’t dumb.  Some of the most proven ones only want to join the next Snowflake or Zoom.  If they truly have it all, they will wait for that shot.

But the most self-aware stretch VPs of Sales know they aren’t going to get called up at Zoom, so they look for the next best thing.  And that’s probably one with the raw ingredients of success, without being a total rocketship quite yet:

• A decently enough funded startup (so they can hire)
• With a great CEO they believe in (so they can run)
• With at least a mini-brand (to back up sales)
• With leads.   With demand.

And a great Stretch VP of Sales can come in and see, say, 30%-50% annual growth paired with a beloved product and tons of leads … as an opportunity.

An opportunity to turn that 30%-50% growth into 70%-100% growth not overnight, but over time.  With a few great enhancements to the sales team, and a few thoughtful upgrades to the playbook.

They know when they see the raw ingredients of success, and know if they can turn that into something special.  They don’t run from these raw ingredients not yet been 100% optimized.  In fact, they see the opportunity there.

I remember when I hired my second VP of Sales at Adobe Sign / EchoSign.  It was at a low point.  After a great run before our first VP of Sales, growth stalled.  But Brendon came in as our true VP of Sales (but our second hire) not just undeterred but inspired.  “I’ve never seen so many leads at this stage.  I know what to do,” he said.  I wasn’t sure it was possible.  But he knew.  And he doubled sales in 90 days.

So if growth has slowed down, but you have happy customers, a mini-brand, and leads … don’t hide your other challenges from those VP of Sales candidates.  And importantly, don’t assume you can’t hire a pretty darn good one.  Share the good, the great — and the challenges.

You’ll be surprised that 1-2 stretch candidates are up for that challenge.

A related post on how this happens:

(note: an updated SaaStr Classic post)