So there’s a moment in time I’ve gotten pretty darn good at spotting in SaaS startups.  It’s the moment in time when … a VP of Sales just doesn’t believe.  A few moments when you see it:

  • When about 60 days into the role, they see that it’s so much harder than they thought.  Things just aren’t closing.  That’s on you for hiring them, but it happens.  A lot.  This is especially common when you hire a VP of Sales from a Very Big Tech Company.
  • When times get tougher, and they haven’t leveled up the playbook.  You just have to when things get harder.  The best VPs of Sales have almost all done this this year, in fact.
  • When the competition starts to pull further ahead.  The best take it as a challenge, but the rest often just … get scared.  They think it will compound, and it will only get worse.

I can just see it, almost smell it over Zoom now, in board meetings and other interactions.  When I see them at events.  When I just watch their body language.  A few tells:

  • Blaming marketing, especially for not enough leads.  This is often true, but it’s rarely the root cause of deteriorating performance.
  • Blaming a lack of product-market fit.  Again, there’s often some truth here.
  • Saying they need more resources to hit the same or a reduced plan.  This isn’t how startup sales works.  Rather, you concentrate more leads in the reps that can really sell in tougher times.  More on that here.

But you can’t just let it … happen.  You have to help.  You have to have your VP of Sales’ back.  It’s a tough job.  So you need to help more in tougher times:

  • Join as many customer calls as possible.  Join twice as many as before, and give your VP of Sales a quota.  A number of deals per week they can bring you into, no questions asked.  Deals almost always close at a higher rate when the CEO is involved.
  • Help out with sales ops and insights.  Figure out not just what isn’t working — but help your sales team figure out where your pockets of strength are.  And help them focus their firepower there. They often struggle a bit to see exactly what’s working the best on a relative scale.
  • Get them more leads.  At least a few more.  Do more marketing.  At least show them you are doing whatever you can here.
  • Rest the plan at least once.  It doesn’t help anyone to have a plan no one can achieve.  But nor does it make sense to reset it multiple times. Do it once, sanely.
  • Help them budget.  A mis-hired VP of Sales often spends tons of your precious cash.  So help them.  Help them make sure they don’t.  They often don’t totally get how the budget should work, especially if they came from somewhere with more capital and resources.

Your VP of Sales should worry, even in good times.  It’s a tough, tough job.  And it’s OK to have times when you are less confident than others.

But once your VP of Sales truly loses confidence, I’ve just never seen it come back.


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