We’ve talked a lot on SaaStr over the years about all different types of VPs of Sales.  From Stretch VPs to stage-appropriate VPs.


It’s worth also focusing on a related, high-level point.  Especially if you sell to multiple customer segments (i.e., small, medium, and large) and through multiple processes (in-bound, out-bound, upsell, channel, partner) … you can’t expect your VP of Sales to be perfect at everything.

And surprisingly, many founders do.

Here’s the thing.  Usually:

  • Elephant Hunters aren’t really very good at Inside Sales.   VPs of Sales that have come up through field sales, hunting six- and seven-figure deals … usually are actually kind of terrible at high velocity inside sales for four and five-figure deals.  It’s just too much effort for deals that seem way too small.  They can’t handle all the noise.  And all the endless questions. And the endless hiring to keep up.   And the sheer number of issues and drama around such small deals.  Versus a great VP of Sales that really is focused on inside sales loves it.  Loves being in the pit.  Loves managing a large team, and pushing them all to goals.  And dealing with the same set of issues, and honing the answers, and winning.  And winning fast.
  • Inside Sales Leaders (Often) Leave Money on the Table in Very Big Deals.  Most VPs of Sales that are good at inside sales can also close larger deals — but they often don’t totally maximize the revenue you could, in theory, get.  They want to close faster by nature, and know time is the enemy of deals, even bigger ones.  And so it sounds great when they close a $250,000 deal.  But maybe a VP of Sales out of true enterprise sales, field sales … could have closed the same customer for $500,000 a year.  That may be fine/better if you close two big logos instead of one, though.
  • Inside Sales Leaders Don’t Love Mapping Out All the Stakeholders, Doing Demo-after-Demo, Filling out RFPs, Getting on Jets (When We Can Again). And Elephant Hunters May Spend Too Much Time Here in Smaller Deals. If you are used to managing dozens of inside sales reps, you don’t want to talk to every stakeholder, do a dozen demos, fill out that RFP … unless it’s a crucial deal. But elephant hunters know you have to get on a jet to close the big ones.
  • VPs of Sales Trained in Inbound May Have to Learn Outbound, More or Less.  If your VP of Sales has grown up in an in-bound environment, she may have to learn how to build a true outbound team.  More and more VPs of Sales have done both these days, but the reality is, VPs of Sales that grew up in-bound are rarely great at outbound.  It’s not just “picking up the phone”.
  • VPs of Sales Trained in Outbound May Not Know How to Optimize Working with a VP of Demand Gen / Marketing.  VPs of Sales that have done it the hard way, without many in-bound leads … may not know how best to work with a great VP of Demand Gen.  So — importantly — they may not process all those in-bound leads as well as a VP of Sales trained in in-bound.
  • Many VPs of Sales Just Want to Be Closers.  They Often Aren’t Perfect at Upsell or Customer Success.  Many true closers only want to be involved in the minimum necessary once the contract is e-signed.  On the other hand, VPs of Sales that have also owned customer success often want a broader purview, to own the whole customer lifecycle, including upsells years down the road.  That can be good — but these folks that want to own all the revenue often aren’t as strong of pure closers.

I could keep going.

My real point is to do your best to optimize your VP of Sales hire around your target ACV.  If your average customer is $50,000 in ACV, and you hire a great VP of Sales with lots of experience at that price point … then she may not be as good at $5,000 and $500,000 deals.  But at least she’s optimized around your core deal.

And beyond that, help her … and if she has materially increased sales, well, cut her some slack.  Let her be good at what she does, especially on the path to $10m ARR and Initial Scale.  Put her in her zone.  Then, help her add managers under her that are good at the stuff she is less experienced in.

No VP of Sales is great at every deal size, every type of customer, and every type of sales.  Expecting that is a recipe for frustration.  Even if she kills the plan for this year.  Because you’ll also see all the places she could have done even better.

Note: an update of a SaaStr Classic Post

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