Hiring & Retention

5-6 Years Is About As Fast As You Can Mint a True VP of Sales


Jason Lemkin

We’ve talked a lot about hiring a VP of Sales at SaaStr, and if you hire a stretch VP of Sales (as most of you will) … how much you can stretch.

A related question is — just how quickly can you gain the requisite experience to be a true first time VP of Sales?  I think best case — it’s 5-6 years until you are ready.

Let’s walk through the career path of one of the best folks on my team:

  • Month 0:  Joined as entry-level, most junior SDR.  Screening the lowest quality in-bound leads.  Had about 8 mos. of prior SDR experience at another SaaS company.
  • Month 6: promoted to first SMB rep.
  • Month 9: makes SMB most profitable segment, becomes #2 rep
  • Month 16: promoted to enterprise rep
  • Month 24: closes 50% of top enterprise accounts
  • Month 36: promoted to manager, manages team of 8
  • Month 40: promoted, manages team of 24 at F500 company
  • Month 50: manages even more, #2 manager to VPS at F500 company
  • Month 60: leaves to be VPS at super-hot venture-backed start-up

So that’s 5 years plus about a year of prior SDR experience, or about 6 years total.  He did this all by age 27 or so.  So I think if you are a total rock-star, and you don’t skip steps and really want to become a manager first … you can do it in 60-72 months.  Acquire all the requisite skills to be a true VP of Sales.  And that’s best case.

Screen Shot 2016-01-04 at 11.54.10 AM

If an aspirational VP of Sales tries to do it faster … which they may be able to do if they join a very early stage start-up or one that isn’t super hot … because someone will give them the title … I really wonder if they can acquire all the skills you really need.

In fact, I highly doubt it.  The VPs of Sales I know that skipped steps almost all end up stumbling later.  They don’t really know how to recruit.  Or, they don’t really understand competitive sales.  Or, they don’t really understand how demand gen really works (a common problem).  Etc.

So by all means, stretch.  You can skimp a bit on the # of direct hires she’s made before.  You can skimp a bit on how long she’s lead a real team.

But if she hasn’t been selling and then managing a team for at least 5-6 years … it’s gonna be a stretch too far.

Published on January 5, 2016


  1. Agreed. In fact, I would argue even 5 to 6 years may be too little. Of course, it also depends on the product. If your product is geared towards the SMB segment with a price point of $20 and it’s all churn and burn, that requires less experience and more grit/determination. True enterprise sales leaders, though, who possess not only the knowledge of the dynamics of a complex year long sales cycle but also how to speak to CMOs, CEOs, etc, need far more experience. Reminds me of my personal experience in my late 20s – during a meeting with a VP of IT, I commented I was a “Senior Account Executive.” His response, “Senior? Is everyone else in the company in preschool?” followed by laughter. Sometimes, having a little bit of grey hair is a good thing.

  2. I became head of sales for the first time when I was 34 and have done a couple of IPO’s since. I can tell you definitively that I wasn’t ready when I got the job for the first time, it was a huge stretch. But, I had some great mentors and teammates that watched my back to ensure I didn’t embarrass myself too much in front of the BOD during that first year. Now I spend a lot of my time developing my guys so they know the ropes. It would be nearly impossible to be an effective 1st time. head of sales without a fairy godmother/father.

    1. yes getting a key mentor or two is critical. in fact, I think the CEO should budget for that in the option pool when she hires a stretch VP …

  3. Do you think it hurts/helps if a few of these steps were achieved at different companies (your boss leaves and takes you with him, for example)? And do you think it carries any weight if after SMB rep role you go to b-school, get your MBA, and then become enterprise rep at Oracle/SAP/IBM? Can that enhance your credibility?

    1. Agreed. This is the fastest possible, and probably only if you sell to SMBs, or at least, have an all-inside-ish team one way or another.

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