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  • Greg DeKalb

Hiring for Sales- a cautionary and all too common tale


I’ve seen it time and time again. The Entrepreneur is working at all hours and burning the midnight oil. They’re out there hustling, getting new clients, delivering, perfecting their product… and just when they’re on the fringe of burnout they start to consider hiring a salesperson. Let’s face it, sales is exhausting, time-consuming and requires a very particular set of skills that not all business owners are experts at. Almost joyful, the business owner begins preparing for their new hire. “Someone is going to take stuff off my plate AND generate revenue, what can go wrong?” they think to themself.


Let the games begin!

After carefully running the numbers, budgeting, and strategizing; they prepare to hire their first Head of Sales. This is no small decision as this employee is going to cost at least $100,000 per year plus benefits PLUS commission. They craft a job description, filter through dozens (if not hundreds) of applicants, and begin interviewing. Who is the right fit? What are their values? Are they passionate about the product? Will they align with our culture? Can they be trusted? Do they have an entrepreneurial mindset? Just like dating, it can feel like looking for a needle in a haystack. Before there’s any hope of relief, the business owner has spent dozens of hours narrowing the search and choosing their new sales guru.


So when does this make your life easier?

Now that you’ve found the right person, the real fun begins, right? Well, it depends on your definition of fun. The business owner puts on a new hat: brain surgeon, as they attempt to perform a brain transfusion and dump all of their expertise into their Head of Sales. Countless hours are spend onboarding them.


About now is where the business owner also finds out what they are missing. The new Head of Sales starts to pester with questions like, “What’s the sales process? Where are the sales sheets and brochures? Wait, there isn’t a steady flow of leads?!?” As the business owner gets them set up on the systems, they get frustrated and push it all back onto the new hire to, “figure it out.” They were hired for their entrepreneurial mindset, right?


Off to the races!

And with a brush off, the business owner has left their new Head of Sales to their own devices. Most likely they are spending weeks if not months, filtering through the half-baked strategy and developing the tools they need to really get going. So add another month or two to “get settled”.


Finally, the highly prized Rolodex comes out… only to everyone’s dismay not one contact is quite the right type client for the new business.


Here’s where the business owner starts to get antsy… They start to wonder if this is ever going to pay off. This new employee’s costs are crippling the business so they’d better produce. The pressure builds and it’s only going to be relieved of one thing that happens….


THEY CLOSE A SALE! … Or they don’t.


That’s right, after 3-5 months the business owner has finally been rewarded with new business. Phew! Let’s see if it happens again. And again, and again.


But most of the time, this story doesn’t have a happy ending. The “sales guy” continues to sell just one person, the business owner. They show activity but no productivity. They sell hope and will string the entrepreneur along for months. Ultimately, this cripples the business as the owner keeps pushing the bills back further and further hoping for that big deal that never comes; until they finally pull the plug.


Most entrepreneurs will lick their wounds and get their nose right back to the grid stone convinced that they are the only ones that can sell. Now with a chip on their shoulder that sales is all smoke and mirrors. They’re the only ones that can do it and drudge on for another couple of years… until it gets to be too much and they start looking for someone new to take sales off their plate… Then they fall right back into the same story, only a little wiser and think, “this time it’ll be different.”


Please, don’t lay victim to this story. Don’t put your business and future at risk with one bad hire. There’s an alternative approach. Instead of putting all your eggs in one basket and relying on one person to take over sales, you can get fractional help. By working with AppointmentsIQ you are able to offload the most challenging and time-consuming part of the job- Prospecting! Effortlessly build a pipeline of qualified prospects and never rely on another person’s Rolodex.


No matter where you are in this story, you can write your own ending. Contact AppointmentsIQ to learn how you can get the support and help in just the right dose.