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Crushing your 1st VP of Sales Hire

At Stella Search, we work with many early stage cyber companies. Some of the most interesting founders. We have been early stage CEO's and CRO's.


Yet far too often we see the 1st VP of Sales in a company fail, and those who hired him/her are surprised. And often put the failure on the candidate they selected as many have not recruited and/or managed Sales leaders in their past. Let's go through some common traps CEO's fall for when hiring the 1st VP of Sales. And how to avoid them.

Common Traps:

  • Pattern Matching - A person or strategy that worked at another company will not be an indicator that the candidate will be the right fit for your company, stage or sale.

  • Prior Company Excitement - Yes, we all want people who worked at winning companies. It is also good for candidates to experience failure. But because a candidate worked at Palo Alto Networks or Crowdstrike, that will not indicate whether they will be a fit for you.

  • Not aligning your customer journey with the experiences and ability of the candidate. Is this a PLG motion, developer-led, trial to close, demo-poc-close or other model?

  • Field Sales success does not = Inside Sales success.

  • Not aligning sales cycle and ACV to your candidate's experience.

  • Understanding - can he/she sell themselves, how do you know this?

  • Board referral - Sure these are very helpful. And sure you want to receive them. But have you really pressed the Board Member on how closely they worked with the candidate. Have you spoken to the candidate's prior CEO?

  • Hiring a contingency or success based firm as it is less expensive. Sure this sounds great but you get what you pay for in process and quality. You are entrusting one of the most important hires in the Company to a contingent firm?

What to add to your process:

  • Exercise(s) - Vital to understanding how one thinks, aptitude and fit.

  • Presentation of their current/prior company. Good way to see selling skills in action.

  • Back-Channel references, not just of prior managers. Get to prior reports, peers and customers (ie CISO's).

  • Understand how they will impact your results in 1 sales cycle; include an agreed upon measurement of success during the period of that 1st Sales cycle.

  • Data and Analytics - core to how they make decisions. Ask them to provide examples.

It is never easy hiring that 1st VP of Sales, even if a Board referral. Getting it wrong is very expensive in burn and opportunity cost, your cash window shrinks. And makes hiring the replacement - much harder. Get help and advice where needed as to how to recruit, how to run an effective process and how to sell the role in your company.


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