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  • Greg DeKalb

When is it the right time to hire a salesperson?

I find that there are two camps of entrepreneurs out there, those that are dreading hiring a salesperson, and those that can’t wait to move sales off of their plates. Sales is the lifeblood of your business, but it can also be the time suck of your day. Between endless prospecting, proposals, updating your CRM, and even after-hours networking, no matter the size of your business, sales is a full-time job. And as a busy entrepreneur, you’re already wearing about 5 hats too many.


Hiring a sales department of one can be a rewarding step for your business, but also one that comes with challenges and a word of caution. It’s like having a kid, you’re never really ready, but all that you can do is get prepared. Here are a couple of important insights and steps you can take to help that bundle of joy succeeds in your company.



Have a repeatable process:

The first mistake business owners make is to not have a strong sales process. Before hiring your salesperson, you need to have worked the process, refined it, followed it, and can repeat success. If you as the business owner can’t make the sales system a success, why would your brand new salesperson be able to?


Don’t forget to include yourself in the process! Know what role you want to play and how you fit into the sales cycle. Just because you have a salesperson doesn’t mean that you should be absent from all sales activities. Otherwise, there's a lot of value and relationships you're no longer a part of.


For example, a great time to bring in a salesperson is if you have a network of potential clients, but struggle to find time to engage with them. You might think, if I reach out, I’m not going to have the time and energy to follow the deal through. Instead, you can be the door opener for your new salesperson. Make an intro to your salesperson and hand the opportunity off. Or, give a list to your new sales rep of strong prospects in your network, and let them begin the engagement process. Find your strengths in the sales process, and find someone that excels in the other parts of the process.

Have the right tools:

Your salesperson is going to need the right tools to get the job done, and you’re going to need the right tools to communicate effectively. A well used CRM is invaluable both for your salesperson and for yourself. You’re also going to need resources for prospecting, sell sheets, proposals, presentations, marketing, and messaging. Without the basics, your salesperson is already playing catch-up.

Have a strong pipeline:

If you’re planning on your new salesperson bringing you a full pipeline, you might need to do some research. Often the new head of sales finds out too late that the services they provided prospects in the past are not quite the same audience your services are targeting. Then you’re in for a big surprise. Before you hire, be sure that your pipeline is stacked so they’ll have something to work on, add value, and can see the process in action. It’s going to take time for them to produce and you don’t want sales to slip in the meantime

Have a great cushion:

Sometimes you have to spend money to make money. A great new salesperson may, or may not, provide a Rolodex of prospects but you can guarantee it’s going to take time before they can produce. Plan time for onboarding, testing, and several months of working the process. All while this is happening, you’re still going to have to pay for their salary, benefits, and health insurance. If you’ve got a longer sales cycle, have even more stashed away to be able to comfortably cover expenses.


From a general numbers perspective, think of it this way. Most times when hiring managers are asking about past deals or a rolodex, what they really want to know is, what is your immediate access to meetings? So think of meetings as your KPI. How many meetings does a sales rep need to set, to create how many proposals, to close how many deals, to hit their goal? For example the average inside sales rep makes a $50,000 salary, including commission and benefits, you are investing $60,000. It varies on the organization, but the expectation is usually between 8 - 10 solid meetings a month. So when you take the annual salary of $60,000 / # of meetings in a year, 120 = your cost per meeting is $500. So if outsourcing sales could cut your cost per meeting in half, and provide more flexibility, would you consider it?


There‘s nothing wrong with hiring for sales, but time and time again I will see businesses jump into the hiring process too early and without the right resources in place. If you’re thinking about making that first critical hire, get prepared and set realistic expectations.


If you‘re still in need of sales support but maybe don’t have all the pieces put in place quite yet, Appointments IQ can help. We’re able to guide you through process development and provide recommendations and implement the right tools for your business. And once we turn on that prospecting faucet, our lead generation systems will fill your pipeline so you can build that cushion. If you’re still struggling balancing sales and running your business, Appointments IQ can provide some relief. We’re here to bridge the gap and fill your pipeline, contact us for a free sales pipeline audit to see where your process can get the most value.