3 Reasons You Should Start Your Career in Sales


I wouldn’t say I’m addicted... but I could qualify as obsessed regarding the NPR podcast, “How I Built This.” It has gotten to the point where hitting traffic on the freeway is exciting because now I have a little more undisturbed time to listen.

A few months into my new addiction pastime I began to notice a trend of those who were featured on the show. From Mark Cuban to Sara Blakely to Angie Hicks to Barbara Corcoran, business leader after business leader started their stories in a very similar way… It is what all the trendy tech companies are calling “the grind” but let’s just call it like it is… sales. Mark Cuban sold computers. Angie Hicks went door to door for hours upon hours to make Angie’s List a success. Whitney Wolfe brought pizza to college sororities and fraternities to get users for Bumble. So, yes, sales in this case was appropriately named “the grind.”

Now correlation doesn't equal causation. Being in sales certainly does not guarantee the future title of CEO or successful entrepreneur. Maybe the personality type that is attracted to the sweat of entry-level sales talent is shared with that of an extremely successful CEO talent or entrepreneur (I’d like to think so in the most unbiased way possible) indicating possible overlap.

I’m not a psychologist, so I’m ditching all the science and evidence and speaking strictly to my personal experience through my company (and of course, “How I Built This”) as to why I think starting a career in sales can be one of the greatest building blocks for a successful career.

Starting a career in sales might be the best move you have ever made because:

1. You learn the business.

In order to be a rockstar employee at any company, it is in your best interest to know what the company does. Now you laugh at the absurdity of this statement, but so many times someone starts in a new role without understanding the business. In order to sell something (or at least sell it well) you have to know what you are selling.

In my case, when I first started at Will Reed, I was hired as a Marketing Coordinator. I was charged with marketing to our target audience of high growth software companies and top sales talent. But I didn’t know their pain points, their day to day, or even the platforms on which they operated.

Once I transitioned to being a Talent Recruiter and talked with clients and candidates all day long, I knew what frustrated both parties. I knew what they liked. I knew how to speak their language. Sales helped me understand the ins and the outs of what Will Reed Jobs did and why it was so valuable. It became easy to sell Will Reed because I believed in it.

2. You learn to fail.

Anyone in sales knows what an emotional rollercoaster it can be. One day you’re on top of the world, and the next day you are wondering if you have any intelligence at all or if people have just been humoring you your entire life.

In sales, you will hear “no” often. At first, it might sting a little bit, but the funny thing is that after a while “no” is not an insult; it is a challenge. It is not a major disappointment; it is a“pick yourself up, dust yourself off” opportunity. It is not shame and embarrassment; it is a great laugh with your co-workers and friends.

In life, you are going to fail. There is just no way around it. But from of our greatest failures come the greatest opportunities to learn. Thomas Edison, the inventor of the light bulb, said, “I have not failed. I've just found 10,000 ways that won't work.” So think of failure as… research. You are just figuring out what not to do so you can nail it the next time.

3. You learn your strengths and weaknesses.

Because of the wide array of skills a sales role requires, it allows for an individual to see where one thrives and where one struggles. From strategy to communication to attention to detail, a salesperson must have incredible relationship-building skills while still being highly intelligent in order to accurately convey the benefits of a technical product offering.

Throughout the sales process, you will have to utilize many different skill sets. The golden salesperson has mastered all of the different areas and can execute them flawlessly 99% of the time. However, that is extremely rare for an individual (so don’t worry if that is not you). Often times, a salesperson will discover that they can find the perfect prospect, get them on the phone, but maybe cannot quite get them over the line to close the deal. Some salespeople could sell an ice cube to an eskimo, but right before closing the deal the eskimo realizes he could have gotten his own ice cube off the ground for free all along… thus the deal falls through.

Some jobs target skill sets so specifically that you may never know you are a natural communicator or a “not so natural” strategist. Being in sales will expose where you can improve, but also where you thrive.

All in all, spending time in a sales role helped me learn the value of Will Reed and how to express it well. I learned how to pick myself and dust myself off when things did not go the way I anticipated. I learned how to celebrate victories! I learned where I could improve versus where I naturally excelled.

As of January 2018, I am no longer in a sales role. I moved into the marketing side of the business, which was my area of study in college and one of my passions. However, if I were to go back to the beginning, I would do it all over again. And I’m sure Mark, Angie, Sara, and Barbara would say the same.

I now know “the grind” is an appropriate title because sales is often quite literally the opposite of smooth sailing. But that does not mean it is not fun. Plus, now we the salespeople can weather any storm.

So you can take it from me, or (more likely) from the many successful business leaders who came before me... Starting your career in sales might be the best decision you ever made.