Making Your First Salesperson Successful

In the context of enterprise sale, making the transition to hiring a salesperson is one of the most critical steps in scaling up your startup.  This post follows up after the previous one.  If you haven’t read it, you can get it here. 

Let’s assume you have recruited a senior salesperson with familiarity with subject matter and sales experience.  Once you have recruited her, there a lot to be done to make her successful.   

Make sure you are not making any of the following harmful assumptions 

  1. “If she is really good, she will figure out what to do.”  – don’t make a hard role even harder. 
  1. “She needs to be an entrepreneur like me.” – an entrepreneurial mindset is precious but she does not need to be like you.  Please the previous post. 
  1. “She is an expensive resource.  I expect her to take over and drastically reduce my time spent on Sales.  I have too much going on.” – Alas, it never works, expensive resource or otherwise.  Plus, you should never be too busy to sell. 
  1. “Why would she need handholding?” – It is not about her capability.  You need to do whatever it takes to set her up for success specifically in the context of your business. 
  1. “This is all I can afford for a salesperson.” – Having considered all things, If you have decided that an experienced salesperson is needed, don’t penny pinch.  There are a variety of ways to design the compensation package.  Remember that Sales is like a horse race.  The best horse wins.  No prices for coming second. 
  1. “I have no money left for Marketing.”  Without Marketing cover you will cripple her in a fiercely competitive market. 

Make sure that you do the following to set up your salesperson for success. 

  1. Set up a formal sales pipelining, case review and tracking – it should be led by you. 
  1. Actively help your salesperson resolve objections and hurdles that come up.  Talk to her daily.  
  1. Keep improving your collateral, script, objection handling database as you learn more and more. 
  1. Ensure that she has a strong voice in product design and roadmap. 
  1. Ensure that she never feels helpless when dealing with people within your organization. 
  1. Organise the funds to provide adequate marketing cover and lead generation support.  As mentioned in the last post, a salesperson is only one piece of the jigsaw puzzle. Prioritise this expense.