Two tips for hiring your first salesperson

Note – this post was also featured on

Working at a Startup is great. Its probably one of the most exciting jobs anyone could have, you get to create something from nothing – literally taking a napkin with some doodles on it and turning it into a dream that is about to come true with millions of enthusiastic customers. Unfortunately, somewhere between the napkin-doodle and your 1,000,000th customer, someone actually needs to say “yes, I would like to buy a few copies of that fine piece of software”, and for that  to happen you need  to hire your first salesperson… Bummer.

There is a long list of skills that you salespeople will need and it varies by industry, software type, customer type and so on.  There is also a pretty good chance that you don’t quite know exactly what the sales cycle will look like and you will know many ups and downs before you figure it out.  These ups and downs will also impact your sales team, which chances are will morph and change over time. More than anyone else your first salesperson will carry a gigantic burden and to make it work out you need to make sure you hire the right person to get it all going. When looking for that first salesperson, there should be two MUST items on your qualification checklist that are above all others:

  • your first salesperson must be a Lone Hunter – the one man sniper killing machine type
  • your first salesperson must pass the High Five / Neck Slap test

The Lone Hunter: the type of gal/guy that can get the job done on their own. Many sales people that come from one of the respectable software giants might have impressive number bloated resumes, but this is not the type of person you need (nor can you afford it). Working at MS/Apple/Oracle/CA/Symantec means that these people are used to having many resources at their disposal: large marketing departments, tons of incoming leads, brand name recognition, polished products, support departments, and much more.  You have none of those – you have a product that is just coming out (probably with lots of bugs), no brand name recognition whatsoever, a few leads at best, and a support department consisting of the CEO’s 15 year old nephew (who is also pitching in on QA).  You need someone that knows how to take on a mission and go get it done without expecting the cavalry to ride in every time some little thing goes wrong.  You need a person that can get his own leads, conduct their own sales process, get the customers approval, and bring in the PO.  Yes, technical pre-sales type assistance is fine, but the majority of the burden must be carried by the salesperson.  Look for people that have successfully sold unproven products- they are used to doing this type of work; and equally as important- they are used to the inherent hit-and-miss process that is part of selling any new product.  They are tenacious and are used to calling on many customers before the first one actually buys.  Don’t look for people from one of the big software companies – their black books will be worth diddly-squat when they are selling an unknown product, because their process is more like farming – not hunting. The leads come in courtesy of marketing, and the salespeople know how to farm them.  Its an entirely different skill-set to find a customer out of nowhere, and convince them to bet their good name and money on a unproven product from an unknown company.  Also, chances are high that if you choose a high-flying software giant type salesperson, he/she will get disenchanted very quickly and leave. They are not used to penetrating a market and to the associated disappointments.  They are used to frequent successes & fat commission checks every month, which is something that you will not be able to provide.  Go for the lone hunter – they will get the job done.  A year down the road when your customers are rolling in, then its time for the big-name types.

The High Five / Neck Slap Test: imagine this while your are interviewing Mr. X: you have just finished a long workweek with Mr. X, finally got a decent night of sleep, and went out for breakfast with the family. As you’re about to take the first sip from your triple latte, you spot the X-dude slowly passing by.  What will your first instinct be? to run up and High Five him, or do you secretly wish you had the guts to come up behind him and give him a giant painful Neck Slap? If its not the High-Five, then DO NOT HIRE. You will spend very long days together during the first year of sales, including many ups and downs, many tough crossroads to face, some decisions taken wrongly, and a fair amount of disappointments and disagreements.  The only thing that can get you through the rough times is a team that loves working with each other.  This is true for practically any member of your core team, but its absolutely critical for the first salesperson.  Make sure you enjoy each other’s company – it will get you through hell, which will undoubtedly come. If the love is not there, the team will disintegrate faster than you imagine.

DISCLAIMER: regarding the “lone hunter” metaphor: With the exception of mosquitoes, I don’t hunt (its just so much easier getting my meat in a nice plastic covered package in the supermarket)

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