Three Common Mistakes of a First Sales Hire and How to Avoid Them

Steve LudwigHiring ChallengesLeave a Comment

gemstones lying in the dust

Make it rain, make it rain, make it rain. 

That’s the dream of B2B tech founders for their first sales hire. They will bring in the sales that will bring you stability and breathing room.

Based on our years of experience, research, and conversations with tech leaders—this is rarely the case. And, it might not be the right mindset for long-term success. 

Let’s step back.

You are making money, but it’s all through founder-led sales. You know you need help but are not sure how much you have to shell out to get the talent that you need.

You’ve heard that good salespeople are earning well north of $100K base with the same on top in commission. That’s pretty steep. Unless you are one of those few who have raised enough capital to not care about the costs or are rolling in cash from early sales, that’s a no-go.

So, what do you do? These are three common mistakes B2B tech founders typically make as a response to this situation.

  1. They look to hire a commission-only salesperson, which, if we are honest, is a dumb idea. Check out this blog post for a breakdown of why that’s a bad way to go.
  2. They look to bring someone in on a part-time basis. While it seems like a cost-saving measure, most have found it is not going to get you what you need. Who are you going to hire? Are you going to short cut the selection process because it’s only a temporary hire? This can cost you less in the short term but doesn’t move the business forward. 
  3. Just as bad as the first two, they bite the bullet and make that full-time, expensive hire, but they hire the wrong type of salesperson. The natural inclination is to hire the person with the biggest list of contacts in your target market and let them loose on all those prospective clients. Too often, this approach fails. Typically, experienced salespeople work in mature organizations that have all the support systems, marketing, and processes to help them close a sale. We call this Playbook sales. For a B2B founder looking to make their first sales hire, all of those systems need to be developed, refined, and executed at the same time. This is the role of your first sales hire, the Pathfinder.

These three common mistakes have massive opportunity costs of time, hard cash, and getting you deeper into the marketplace. 

So, what should you be doing?

  1. Recognise the role of your first sales hire is to develop a predictable, repeatable, scalable and profitable sales process. Yes, they have to help land clients, but within the framework of developing the Playbook that will underpin building a scalable business.
  2. Make sure you’ve got the business solid enough to ‘carry’ your new sales hire for a year. It doesn’t mean they won’t generate revenue, but that first year is really the time they need to build the sales cycle.
  3. Ditch the notion of hiring a Flashy Pants salesperson at an exorbitant salary and start looking for “diamonds in the rough”. These are people who are not necessarily in front-line sales but who have the capabilities to be successful in sales and who have the right [Pathfinder] mindset to be successful as your first sales hire. 

History shows that Pathfinders have the right vocational skills and mindsets to be successful first sales hire for startups.  These include:

  • A strong ability to deal with ambiguity. The first Sales hire role is one without a Playbook and, by definition, such an early startup lacks the support (e.g. lead generation) of other later-stage companies.
  • A willingness and excitement around building the processes and procedures necessary for a successful Sales operation as an organization scales.
  • A curiosity that allows for creative solutions.
  • A hunger motivated by something quite different to most other Sales types. We’d characterise this motivation as intrinsic rather than extrinsic.

So, how do you go about finding these Pathfinders? The Right Five has developed a simple process that allows:

  • Quick and painless hiring process: The Right Five automates the candidate assessment/scoring/communication leaving you simply with the selection of those Pathfinders you want to interview.
  • Fast on-ramping: Because your first Sales hire needs to be a Pathfinder (the clue is in the name) their need for on-ramping is minimal. It’s their job to develop the repeatable Sales process that will allow you to scale, so they won’t expect red carpet treatment.
  • Reduced risk: The Right Five reduces the risk for you because our online assessment/rules engine identifies Pathfinders, i.e the candidates who will be successful as the first Sales hire.

Want to find out more? Watch this five-minute overview and demo of The Right Five or send us a note and we will set up a meeting.

Curious to know more about the assessment? Want to see if you are a Pathfinder? You can take the assessment here for free but make sure you check out the notes at the bottom of that post before you start. Your results are yours, we don’t share them with anyone.

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