De-Risk Your Sales Process With Better Hiring

As a sales guy, I’m pretty familiar with the various negative stereotypes of salespeople that exist out there in the world.  When many people hear the word “salesman”, after all, their brain immediately conjures up the classic image of a skeezy guy with a bad suit standing on a used car lot.  They picture a person with shifty intentions doing whatever he needs to do and saying whatever he needs to say to get the customer into a car and off the lot so he can move onto his next victim.



Those who work in and around startups might have an equally negative but different idea of what salespeople are like, instead picturing a group of dumb guys standing around the foosball table at the office all day.  Unfortunately, a lot of folks assume that people get into sales because they want to work at a startup but lack the programming skills necessary to participate in a technical way.

This is simply not true.  I’ve worked in sales long enough to tell you that there are plenty of driven, smart and resourceful people working in the field.  If you’re a startup founder looking to hire a sales team, you’ll be surprised by the diversity of knowledge and experience that the right salespeople can bring to your company.

Of course, the right salesperson will be different for each company.  You’ll have to ask yourself a number of hard questions in order to figure out what kind of salesperson you need.  Doing so will help you to build a more sustainable (and far less risky) sales process.


What Kind of Person Does My Sales Team Need?

Because there is such an array of salespeople out there, each with varied experiences and skillsets, you’ll want to find the ones that are most equipped to sell your specific product.  After all, you’ll need to make sure that your sales team is prepared for the phone calls and meetings you’ll be sending them into.  

In order to know what kind of people to look for, then, you’ll want to ask yourself a few key questions about your business.


Do We Deal in Transactional Sales or Complex Sales?

If your startup is at the point where you’re hiring a sales team, you’ve probably already done enough sales to know whether your sales process is complex or transactional.  For those of you who aren’t familiar, transactional sales are the type of sales where the buyer can just swipe their card and send you off.  Whether it’s during the first, second, or third meeting, transactional sales are the type of sale that doesn’t require the buyer to speaker with their partners before they make a purchase.

Complex sales, on the other hand, are not as easy of a process.  Complex sales take place in an environment where you have three, four or several decision makers involved in the buying process.

If you know that your sales are going to involve the Head of IT, the VP of Sales or any other higher-ups at a company, you want to have salespeople that are prepared to talk to those folks.  You don’t want hire a salesperson who’s only dealt in transactional sales to be overwhelmed by a more complex sales process.  


Are Relationships Necessary for Us to Sell?

Your company may have a sales process where you can only sell to people who already know you.  In this case, your salespeople will have to have preexisting relationships with your potential customers.

If you’re dealing in million dollar media contracts, for example, there are only a few companies buying media in that large of increments.  Typically, these companies only buy through ad agencies, so your sales reps will need to have prior rapport with those agencies.

For these reason, many startups hire their sales employees based on who these employees have in the Rolodexes.  The right sales team could possibly be the only way to get you into a meeting with the companies you want to sell to.


How Much Does Our Product Cost?

Your sales reps have to be prepared to ask for the amount of money your product costs.  If your device or software costs over $100k, you need to have a sales rep that is capable of confidently saying that number to the buyer.  In the past, I’ve worked with reps who couldn’t believe that they had to ask for the amount of money they were going to have to ask for.

Remember that there are people out there right now who are trying to figure out how to spend a million dollars on a product.  Understanding what their environment looks like, who their boss is and how they decide to spend so much money will be infinitely valuable to your sales process.  Having a sales team that has lived through that experience before will only increase your chances of moving your product.


Who Are We Trying to Sell To?

Your Ideal Customer Profile (ICP) is something that you should have a good grasp on by the time you’re putting together your sales team.  You should have a good understanding of the person that needs your product more than anyone else.  What is their job title?  Who is their boss?  What is the shittiest part of their job and how can your product make their day easier?

Having a grasp on your ICP is not only necessary for your business, it is something you should use to hire sales reps.  Salespeople who have experience selling to certain job roles will have an understanding of that person’s pain points.  They’ll probably also come to your company pre-equipped with insight on how to navigate your target companies.  


What Is Our Sales Cycle?

The sales cycle of every startup is different.  Some companies take a only week after their initial meeting to sell their product while other companies have a much longer sales cycle.  If you know that it’s going to take 90 days, with a month just to get the right person on the phone and another two months to work through the rest of the sales process, you can use this information to hire and structure your team.  

Tip:  Find People Who Have Experience in the Role You're Looking For

Don’t forget that there are multiple roles one can perform on a sales team.  On the average sales crew, you’ll usually see a Marketing Development or Lead Development Rep, a Sales Development Rep, and Account Executive, An Enterprise Executive and a Sales Manager, Team Leader or VP of Sales.  Most of the time, you’ll see multiple people doing some of these jobs.

Taking into consideration which aspect of sales your potential employees have done before is crucial to hiring the right person.  Just because someone comes to you with experience as a Marketing Development Rep doesn’t mean they have the skills your looking for.  While this person probably has a background that could be valuable to you, their experience might just be in finding phone numbers and scheduling meetings.  

They’re not necessarily the person you want to put in a chair across the table from your potential clients.

Do your homework.  Find out to what extent they have experience selling, how much they were selling for, the length of their sales cycle, etc.  


How Do I Know If I’ve Hired the Right Sales Reps?



In my opinion, the best way to figure out if your sales reps are a right fit for your startup is to give them the same targets.  Determining what those targets are will depend on your company, your ICP and the way your sales process works.  Whatever the targets end up being, having both (or all) of your reps aim for the same goal is the easiest way to figure out if they’re rockstars or duds.

For this reason, I always recommend to founders that they hire reps in pairs.

This doesn’t, however, mean that you need to pit your sales reps against each other like dogs.  Hiring two sales reps can actually be the opposite.  Instead of simply incentivizing competition, it gives your reps a network of support that they can use to bounce ideas off of people and find better ways of doing their job.  

In the end, after all, hiring a sales team is about building the company culture that’s most conducive to a productive and profitable business.  While you want to hire skilled individuals who are capable of doing what you need them to do (as opposed to just hiring the people you want to play foosball with), you also want to avoid structuring your sales process like a wrestling match.  While there are good ways to set up incentive structures, they sometimes promote a company culture focused on quick payments over company growth.  Remind yourself, as you start to hire reps, that sustainability should always be the goal.  This will help you to avoid turning your startup into a used car lot.  

Ryan Williams