Critical Criteria When Hiring A Salesperson

Whenever I analyze a salesperson for a job, I first apply the lens of whether she fits the role.  There are four possible sales roles:

1. Existing products to Existing customers

This is the easiest type of sell.  Not saying it is easy.  Just the easiest of the four types.  It is the easiest because the key to sales is trust.  The first rules of sales is that clients buy from people they like and people they trust.  That’s just how it is.  So when you hire a person to support/sell to an existing customer, the trust is already established.  Now the salesperson still has to maintain that trust and be likeable.  But she starts in a good place.  On the Hunter-Gatherer spectrum, these salespeople are considered Gatherers.  Note, this label is neither a negative nor positive, just a statement of the role and skill set.

2. New products to Existing customers

This is next in order of difficulty.  But again, trust is already established with the customer. Therefore, the same salesperson as in role #1 can often fill this role.  It is certainly a more challenging process than #1 because the salesperson needs to uncover needs and budget, etc.  But since she already has a trusting relationship established, the salesperson can navigate the client’s organization to get this information.  This is hunting, but in a friendly forest.

3. Existing products to New customers

This role is orders of magnitude more challenging.  As you can guess, the key is still trust.  There is no established relationship yet between the sales person and the buyer. Often, the first meeting is the first time that the customer was introduced to the salesperson.  But the good news for a salesperson in this role is that since it is an existing product, some level of trust has already been established, ie trust of the brand/product.  The salesperson has to demonstrate an ability to find the decision maker, budget holder, need, etc.  Also be able to fight off competitive challenges tactfully. The salesperson has to be able to deal with all kinds of issues in an environment which no one is fully on her side…until the deal closes.  A salesperson has to find the internal support and manage that person/people like oxygen.  This is a pure hunting role. The salesperson has to relish this high risk, high failure environment.

4. New products to New customers (aka startups)

As you would expect this is the most challenging sales role, by a wide margin.  Not only does a salesperson have zero trust yet with customers but her company is actually distrusted due to its newness.  The first hurdle to cross is “I have never heard of you.”  A company has to cross that for the salesperson by solving a real pain point or doing something radically better than an incumbent product.  The brand name should be professional and the product should look like it is real.  These are no small challenges for a startup. But if the company cannot cross these hurdles, then a salesperson can’t either.  This is one of the key reasons that the founder has to be the first salesperson.  If a founder can’t sell her product, NO ONE else can/will.

Once this barrier is crossed, the salesperson still has a ton of hard work ahead of her.  This is hunting in its rawest form.  I mean war paint on your face, dropped in the middle of unfriendly forest type of hunting.  This type of salesperson has to thrive in an extreme failure/extreme risk environment.  The key skill here is figuring out who the right customer is.  Simply put, most customers will not use a startup’s product no matter how great the pain is or how cool the solution is, because of the reputational risk due to an abrupt shutdown.  The salesperson needs to find her initial customer sponsor, uncover information and then figure out how to navigate the rest of the organization.  And while the company established some credibility with the initial lead, the fact that the product is a startup will come up over and over again.  A salesperson has to constantly sell against that risk at every level.  Competitive products will come up over and over again.  Often referencing competing products is just a cover for “let’s not take the risk on a startup.”  A salesperson in this role has to be great at building a large pipeline, because the close rate will be lower than normal.  The salesperson has to be an extreme self-starter.  No one is going to navigate the day for her.  She has to be hungry.  Have a fire in her belly.  Be passionate about her product and the market.  Be knowledgeable too, because the detractors in an organization are going to throw a lot of stones.  She will consistently find herself in meetings where there is a very vocal critic.  Just looking to kill the deal.  That person is often scared of something new, which translates into work for him.  And he will work really hard to avoid learning a new product.  So the salesperson has to be a bit of a psychologist too.  To find a way to make that person feel comfortable.  She can’t fight that person.  Angry becomes transparent.  She has to kill him with kindness, supported by facts.  Remember, people buy from people they like and people they trust.

The most important action a salesperson in this role can take is to land a reference-able customer.  Someone who is credible and willing to be quoted publicly.  This reference will be used over and over in every subsequent sales meeting.


When hiring a salesperson for a role, I believe that that person has to have demonstrated these capabilities in past roles or demonstrated the right skill set.  It is important to be open to the challenges with the candidate.

Far too often a salesperson from role #3 will leave a big company and go to a startup (role #4) thinking the skill translates..only to flame out.  Certainly some skills translates, but that salesperson has to understand that the challenge is materially greater.  To me, the key to a great sales hire for a startup is not only skill set, it is passion.  Passion for the product, passion for the challenge ahead of her and passion for working with the team.  Ask yourself, has this person demonstrated the passion needed to overcome the extreme ups and downs.  Is she a fighter?  What motivates her? If she is motivated only by money, as many salespeople are, then do NOT hire that person into a startup.  People who are motivated by money are also very, very unhappy with quarterly cash flow swings.  Chasing the gold ring is fine so long as her downside is protected.  And a startup simply can’t guarantee that.  Sure, money is an important factor for everyone.  People have to live and pay bills.  But to overcome the extreme ups and downs of a startup, the sales candidate has to have a true passion for the mission.

Published by v1again

I try very hard to be a great father, husband and entrepreneur. Founded and sold 3 companies. is my 4th startup.

One thought on “Critical Criteria When Hiring A Salesperson

  1. in my business they just have to be smoking hot a pinch flirtatious and can count to 10…

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