Are you ready to hire your first salesperson? Here’s how to do it

ready to hire your first salespersonHustle is your middle name. You’ve been pounding the pavement, dialing for dollars, and bringing’ home the bacon. All that new business activity has built some small success for your business — a few employees, a real office. The business is feeling like less of a struggle. All that is good.

But this new growth hasn’t made your life any easier, in fact it’s gotten worse. Now you have to sell twice as much, and the pressure is getting to you. “How can I be the leader of this team if I spend all my time selling? It’s time to hire a full-time sales person, right?”

You are likely right, a sales person should be your next hire. But there are a few things you need to do to first to insure that your new sales person has a fighting chance of being successful. If you rush out, hire someone who “looks good”, and turn them loose on your prospects–only to find out 3 months later that they can’t get the job done, the pressure is going to be even worse. It’s worth it to make sure that this first hire is a good one. So here’s some homework you need to do before you start searching for someone:

Document your sales process

When a business owner does sales it’s usually a pretty organic process, we’re hustlers. We have a very intuitive sense of where the prospects are that we want to work with, we have the experience and judgment to assess those prospects and then we often “bend” our services to fit the needs of that prospect — doing a little wheeling-and-dealing at the end to close the sale.

It’s unlikely that you are going to find a sales person who can do all that. They aren’t going to have your credibility (as President of the company), nor your price flexibility. They may not have the experience of delivering the services, so there’s risk that they might “bend” your services to fit in a way you can’t deliver. So we need to build a sales process that doesn’t rely on those things, that doesn’t require you to successfully run it.

To do that we need to document, write down on paper, what the buyer’s journey looks like. When does a prospect realize that they have a need for your services? What issues do they face? Who is there to “witness” that, or who do they call for advice? Then what information do they need, what options do they consider? What makes them ultimately buy from you? You know all of this intuitively, but you might be surprised at the clarity that can come from writing it down. Documenting this process provides you, and your sales person, a roadmap of how to get a prospect to become a buyer.

The second step is to listen to yourself as you are selling. Are there things you say over and over? Ways you’ve explained the value of what you do that help prospects to get it? Write them down. If you can, create a script for how your sales meetings go (ideally). I know every one is different, but if you look at 4-5 that were successful, what happened in each of them?

By writing this down you now have the beginnings of a training plan. Yes you are going to hire someone who knows how to sell — but you need to teach them how to sell your business and you are the expert at that (so far).

Define Roles

What role are you expecting this new sales person to play? Do you want them to be a mirror of you, totally independent, sourcing their own leads and closing their own deals? Or are you looking for someone who would be a team member with you, someone who could do some prospecting, set appointments for you, write the proposals and do the paperwork so that you can get in front of more prospects and close more deals?

In most businesses, and I’m including businesses with Billions of dollars in sales, the President or Owner is always going to be the best closer. No one has the credibility, pricing flexibility, or clout that you do to close a deal. If your goal is to grow your company, without burning out, the lowest risk approach is to hire an inside sales assistant — someone who can help you to sell more, who can learn the clients and the business and then eventually move out in to a full outside sales role. Trying to hire someone to mirror you, who can blaze their own trail, find and close their own business, is a much more difficult, and riskier hire.

Try to capture this thinking in terms of a Job Description. It will be helpful now as you are hiring, and it’s also a great tool for performance management later.

Develop a profile of the successful candidate

Now that you have clarified what role you want this person to play — what type of person is this? Create a picture in your mind (and on paper) of the characteristics of people you have seen be successful in this role. Talk to other business owners who have hired sales people — ask them what they have seen be successful.

It’s important to be realistic here; you don’t want to be looking for Wonder Woman — she’s hard to find and if you do find her she’s very expensive. So be careful when you are imagining “a big picture thinker who never misses a detail”. Do you need more of a big picture thinker, and you can provide admin support to deal with details, or are details imperative and you can give up some of the “big picture” strategic thinking? You need to work to identify traits that would make this person successful in the role you have created.

Consider the trajectory they’ve been on. What does a track record of success look like? Do you want them to generate leads? You need to see experience, and success, prospecting. Do you need them to navigate a complex buying process with multiple stakeholders? Make sure that they can show you how they’ve done that in the past.

Plan your hiring process

Remember that job description you made? Look at it again, and make sure it captures the role in detail. Now, using that job description, and thinking of your ideal candidate, create a job posting that is likely to attract the kind of person who will be successful in that role. The best way to attract people who are up for a challenge is to make the job appear challenging in the job post! Don’t soft pedal it, lay out the challenges and opportunities as clearly as you can.

Job Boards can produce a large volume of candidates, and if you need to hire quickly then they are a must. But there are some other ways to find good candidates. Look at who’s selling to you — see someone who’s got the skills you are looking for, ask if they are open to a move. Put the word out to your customers, vendors, and referral partners — people who know you best will produce the best candidates.

Once you have candidates how will you evaluate them? Interviews, without a written interview guide, have about a 50% success rate. If you want to improve that, create a written interview guide and use it for every candidate. Ask about their past jobs and past bosses. What challenges did they face there? Also ask some behavioral questions and make sure they can give you examples of times that they have demonstrated the traits that you are looking for. One of the best sales hiring processes I’ve seen is in the Chet Holmes book The Ultimate Sales Machine (see Chapter 5).

You may feel like you are at your breaking point, and instead of giving you help, I’m giving you homework (and you’d be right). But I can assure you that not doing your homework and making a bad hire is going to put you much closer to the breaking point than you would be if you slowed down a bit now to do this right.

Sales Call to Action


  1. Brad, you’ve not only laid out a great way to hire a salesperson, but the process you’ve presented is perfect for hiring anyone in a company, really! Thanks much for this resource. – Mary-Lynn, BIGG Success

    • Mary-Lynn;

      It’s true! This could work for any position. I just know that this first sales person is such a critical hire — if folks aren’t willing to do it for every position AT LEAST do it for this one.

      Thanks for commenting.

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