Navigating the hardest hire you will make – your first salesperson


So you’re ready to hire the first sales person for your startup.  Two questions that you will inevitably ask yourself:

1. )  Why is hiring salespeople so difficult?

2. )  How do we pick the right salesperson?

Let’s dive into both:


1.)  Hiring salespeople is hard for a few reasons:

  • Even mediocre salespeople are really good at selling themselves.
  • Salespeople are a product of their environment.  Just because they were effective at selling software for X company with all of the resources that X company provided, doesn’t mean they will be effective in your startup environment.
  • Great salespeople are always in demand.
  • Great salespeople that are making good money have a really hard time leaving those jobs.


2.)  Steps to follow to ensure you are hiring the right salesperson:

  • Sell the opportunity.  Make sure that you are selling your startups vision and long term potential in every conversation.  They are not just selling you – you are also selling them on why they should take a lower salary than they could obtain elsewhere.
  • Run a structured interview/selection process that uses objective scoring in each step and don’t rely solely on your gut feeling.  (I happen to know of a great tool that can help with this….
  • Ask them to provide you with their W-2 from the last 3 years.  This will give you a good indication of how successful they were and what percentage of their compensation came from commissions.
  • Have them prepare a 90-day achievement plan.  What will they do in the first 90 days to make them successful.  This can help you gauge their motivation and excitement about the role.  It will also give you some insight on how they will approach the position.
  • Compare them to their peers.  How did they perform and stack up to the other salespeople in their past roles.
  • Run structured reference checks.  Make sure to ask past supervisors to clarify their performance and achievements.
  • Focus on their past environments.  Why were they successful in past roles?  What resources were they provided?  What were the sales cycles like?  What level decision makers where they selling to?  Get this information and compare it to what they will encounter in your environment.


One parting note:  Who should  your first sales hire be?  Should it be the eventual VP of Sales?  Or, should it be someone to cold call and find new opportunities?

At Hireology we tend to hire the person that leads the department first.  That person helps create and shape the department.  Strong ownership of that department typically follows.

This all depends on resources however.  If you can’t afford that person early on think about a performance based equity plan.


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