Top 10 Mistakes I See New VP’s of Sales Make The First Week on the Job

 

So lately I’ve watched a lot of new VPs of Sales and CROs crash and burn when they start.

Is it their fault?  The CEO’s?  The VCs?  Sometimes, there’s some finger pointing here.  But it really doesn’t matter in the end.  It was an mis-hire.  And that’s tough on everyone.

And one thing I do know is a lot of mistakes are avoidable.  Avoidable by the CEO making the VPS/CRO hire.  And avoidable by the candidate, truly understanding if it’s a good fit.

You’re going to possibly laugh at a few, but here are the Top 10 Mistakes I’ve Seen New VPs of Sales Make The First Week on the Job.  The ones I’ve seen recently.  And it’s also a checklist of what to avoid.

#1.  Not Knowing the Product Cold Before They Start

Many founders won’t push here.  They’ll be charmed by a VP of Sales talking about process (lots of process talk), team building, and talking about how they’ll level things up.  But so many VPs of Sales start far, far behind the eight ball when they think they can learn the product on the fly.

#2.  Not Starting … Before They Start

VPs — start the week before you start.  Get going on email, on Slack.  Listen to more calls.  Quietly be added to cc lists.  Watch recordings of team calls.  You don’t have to literally be on Zooms before you start.  But on Day 1, don’t be spending all your time setting your G Suite and figuring out the tech stack.  The best start before they start.   I recently watched a VP of Sales show up at 10am their first day, having not even logged into email first.  No chance.

#3.  Insisting It Be Done Their Way

This is a tough one.  Of course, as a sales leader, you have your way of selling, a way of managing, a set of systems and processes you were taught and came up in.  And the startup you are joining almost certainly has different ones.  Way too often I hear a brand new VP of Sales say something like, “We’re not doing it this way anymore.”  Often on Day 1.  Look it’s OK to think that, and it’s OK to rapidly level up the team.  But first find what’s good in what’s working.  If you’re joining something that’s already growing quickly, slow it down and learn what’s working first.  Before you change anything.

#4.  Having No One Lined Up to Join Them

This is an OG SaaStr post, point and theme, but as true today as ever.  There’s almost no chance to hit the ground running as a new VP of Sales if you don’t have a few reps you trust and know are strong set to join you quickly.  Not always on Day 1, but quickly.

#5.  Not Asking Enough Good Questions.  And Not Being Curious Enough

Way too many VP of Sales candidates these days try to (1) turn every interview around to interviewing the founders back and (2) talking all about process.  I see so many candidates basically run this playbook when interviewing with CEOs and board members:  “So, tell me more about the company.”  Lazy.  And then bring out a Powerpoint deck they’ve used before on how they scale hiring. From 8 reps to 16 to 64, territories, etc.  The process slides are always awesome looking and sound like what you need.  But it’s not remotely what you need.  You need a great hands-on exec with a curious mind.  That really wants to learn why and how customers buy, and has already done a lot of homework in the space.

#6.  Not Starting Outbound on Week 1.  Or at Least Some Outreach

Ok some may disagree with me partially, but the best VPs of Sales do some outbound their first week.  Maybe not a structured program, but at least they start reaching out to some folks in their network.  Some folks in the industry, etc.  They start to reach out to some potential prospects that aren’t already in the pipeline.

#7.  Not Being Able to Demo the Product Themselves

You gotta get there in Week 1.  Week 1.  Or you probably never will.  There’s nothing wrong with having sales engineers, solution architects, and all that in some sales motions.  But if the VP of Sales never learns to demo the product for real in Week 1, they almost never do.  How do you teach if you can’t do it yourself?  These VPs of Sales again end up being all about process.  But they rarely can be allies of the customer.  Because they don’t know.  It also proves you can meet the first criteria / point above.

#8.  Not Understanding the Existing GTM Motions

I see a lot of VPs of Sales that for example have only sold direct not understand a selling motion that also has a big partnership or channel component.  40%-50% of Shopify, HubSpot, etc. revenue comes from agencies and partners.  So many VPs of Sales don’t really understand how this all works before they start.

#9.  Wanting to Go More Enterprise Immediately

There’s no question for most SaaS companies, going more upmarket is something you’ll eventually do.  It’s a big theme for the public SaaS companies today, even folks that have historically focused on SMBs like Monday and HubSpot and Asana.  But it’s not always the right idea on Week 1.  If 90% of the revenue is from SMBs, maybe learn that motion first.

#10.  Not Truly Understanding the Ecosystem You Play In

A variant of the prior point.  But you’ve got to go deep on the ecosystem to win in many cases.  If you’re a Zendesk partner, you should be there on Week 1.  Not … learning how Zendesk really works around Day 100.  Again, way too many VPs of Sales think they can wing it.

Look it’s a tough job :). There’s so much to learn, so quickly.  If nothing else, learn as much as you can before you start.   Too many wait until they start to start learning.  And that’s often at the edge of too late. 

Trust me.

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