Hiring over your head of sales – When the suit outgrows the wearer.

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Let me start by saying that if done right, hiring over the top of an existing head of sales should be a VERY positive thing for both the business and the incumbent. This post tells you when to do it and how to do it:

Do it before your head of sales loses their shine

The key to making sure that this transition goes well is to do it before the situation becomes dire. Imagine your head of sales is in quick-sand (they kinda are) and you can see them sinking – Your new CRO or SVP is the hand that pulls them out. If you wait until their head disappears it is too late.

It is time to hire over your HoS when:

  • They are unable to articulate a clear and milestone driven sales operating plan that gets you to your next annual target.
  • You are observing that they are not able to contribute to the strategic plan in a way that secures buy-in from executive peers
  • They are ‘too busy’ to get the scaling infrastructure or hiring done.

You have left it too late when:

  • Your individual contributors are leaving, citing job dissatisfaction.
  • Peers to the HoS have lost respect for him/her
  • You are unable to meet your hiring plan

Hire someone who has seen the next phase and coached to greatness

In hiring over your HoS it goes without saying that they must walk in with a ‘first principles’ understanding of how to take you to the next stage (See my favorite post on the subject by Jason Lemkin). What I see people miss is that this next person should be a great developer of people and careers. Your HoS got you to where you are and I am sure sweated blood to do it – It makes both moral and business sense to find them a leader who can take them to the next level.

On the subject of hiring well, be sure to test that your new sales leader reallyunderstands what they are talking about, rather than reciting the glossary of terms. To get to the heart of how to do this, check out this Farnham Street blog post, which explains how to test for ‘first principles’ understanding, which is a soap box item of mine.

Through most of our life we get through it by reasoning through analogy, which essentially means copying what other people do with slight variations – Elon Musk

The best sales leaders I have worked with owe much of their success to being open to coaching and absorbing new skills/behaviors from people who have walked the path before them. By hiring the right leader you will not only solve your immediate challenges, but also provide your existing manager(s) a wonderful growth opportunity that will build both capacity and loyalty.

Meet the Author

Matt is the managing partner at SalesOps Central and founder of SaaSy Sales Management, Silicon Valley’s Sales Management training and leadership community.

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