The Perils and Pitfalls of the “Been There, Done That” VP: Posers and Mercenaries

{Part 2 of our series on Start-up Hiring}

Basically all of the SaaS CEOs/founders I know of have made at least one terrible VP+ level hire.  Sometimes it’s VP Sales (OK, often, this is the most common mishire — another post here on what a really great VPS can do for you, and how a poor one can wreck your company, coming).  Sometimes it’s VP Marketing.  Or VPE, or whatever.

Different companies, different positions.

But one common thread — the mishire seems almost always to be the Great “Been There, Done That” VP.  The Great Guy from Salesforce (often, due to its scale), or whatever other leading SaaS company.  Or sometimes, from a successful SaaS start-up with a high profile acquisition.

The Guy (or Gal) that “Took Them From $0 to $100,000,000 in Revenue” or “That Scaled an Entire Dev Team from 1 to 100” or “Got Us On TechCrunch 7 Times in 8 Months” or whatever variant thereof.

The problem isn’t that this hire is a Unicorn.  In fact, there are plenty of them out there.  The problem is They Never Work Out.  Why Not?

  • First, Most of Them Didn’t Actually Do It All.  Success has many fathers, and many more hangers-on.  So test the proposition.  Did that guy really close the Top 5 customers him/herself, singlehandedly?  Or at least generate the lead?  Or honestly — ever even meet the customer?  These guys are often great schmoozers and have perfected that art of selling up.  You’ve been warned.
  • Second, If They Really Did Do It All – Why Would They Join You?  You’ll Have a Mercenary On Your Hands.  This is the subtler risk, when you do in fact lure than Unicorn in.  If your start-up is even reasonably hot, you’ll eventually get a few folks who Actually Did it All to at least take a meeting with you.  The problem is, if they really did it all, why would they join you?  The #1 reason to do a start-up is Career Development.  But if they already developed their career at a “better” company, what do you have to offer?  Only money.  Only the hot stock in your hot start-up.  That’s great when it’s hot.  But the problem is, it may not be hot every day.  Even worse, doing your start-up is actually going to be a lot harder than their last company, the Big Success.  So They Will Quit As Soon as it’s Hard and As Soon As They Doubt They Will Clearly, Easily Make Millions.  Look at all the fancy resume exits from Zynga lately.  They look like mercenaries to me. Mercenaries leave when the war gets tough, because the pay (the equity) can’t keep up.

So what’s the learning?  You’ve got to take a calculated risk of some sort.  You have to hire VPs that are in some way, not the complete 100% package, not every box checked.  You can go for folks that will get to 100% in your start-up (my vote) by making it a success.  Someone on the way up.  Or you can go for folks that are almost great, with a little more experience, but damaged somehow, something that stopped them from ever fully getting there.  And you can backfill the damage and gaps.  The latter generally have a better resume than the former, and feel less risky.  Though I think they are riskier.

Either way, I’d pass on Been There, Done That.

schmoozer image from here.


  1. Brendon Cassidy

    So what happens to that guy you get on the way up, after they succeed? How about a new category called “Been there, done that, but don’t really care that they did that”? 🙂

  2. Hiring is tricky period. Anybody that claims to have a 90% great hiring track record either hasn’t hired many people, hires the same people over and over, or is so picky they’ve missed opportunity because it takes them 6 months to hire the “right” person.

    Having someone try to duplicate their previous successes often results in “me too” marketing, and big disappointment. I look for natural marketeers, because almost anything can be learned. The question is how much time do you have? I’ve had the best luck with smart, loyal people with a great drive to succeed, willingness to learn and fail, and someone who will actually execute on a plan.

    Full disclosure, I’ve been there, and enjoyed a successful career. But have also not done so in such a highly visible operation that the world flocks to my door. (I agree with the “It’s all about the journey” comment.)

  3. Mark Organ

    Holy cow this blog is awesome. This man speaks the truth. With devastating clarity and frequency.

    I agree completely on hiring people on the way up. People need to be excited to come to work everyday and usually that is because they are learning and growing. I’m a big fan of cross-pollinating too, bringing on someone in a sales role who used to run marketing, for example to round out their skill set. A rockstar can play second base and shortstop just as well.

    Learning is a drug. It is the #1 thing I solve for at my companies and for how I spend my time too.

  4. For sure. I realized the other day you can telll someone who thinks Learning is a Drug when they can describe to you a seemingly successful position they were in when they were Bored. 😉

  5. Pingback: What a Great VP Sales Actually Does. Where The Magic Is. And When to Hire One. : Enterprise Irregulars

  6. Pingback: What a Great VP Sales Actually Does. Where The Magic Is. And When to Hire One. : CloudAve

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