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Advice / Career Paths / Exploring Careers

What to Consider Before Becoming a Road Warrior

If you’ve ever been an office dweller, you know how all that florescent lighting can mess with your brain. What you wouldn’t give to be one of those traveling salespeople, cranking the tunes in a company car and sporting a tan acquired from leisurely rounds of golf with rich clients! Not to mention the home office, the flexible schedule, and all those frequent flier points.

Those were my thoughts eight years ago. Stuck in a safe but boring corporate job, I’d somehow found myself in information technology. What had happened to my dream of conquering the fashion world? Scared by the idea of a future of pocket protectors and pleated khakis, I eventually made a jump and landed a job as a traveling sales rep—or “Road Warrior”—for several lines of women’s activewear. Finally, I was going to have the glamorous career I so richly deserved!

Fast forward one year later. I was broke, miserable, and again looking for a job in my unsexy but lucrative IT field.

So what happened?

My first mistake was becoming an independent sales rep. This meant I had to pay for my own health insurance, my own car, my own insurance, all my gas, and all my travel expenses. (Oh, and all of the clothing samples I was selling.) I quickly learned that clothing sales was not the glamorous job I had thought it would be, and it sure wasn’t easy to cover my expenses.

Of course, you may be thinking, “Well, then I’ll get a sales job that gives me a company car, insurance, 401(k), and a cushy expense account. And it won’t be a problem—I’m great at it!”

Maybe so—but there’s still a lot to consider before taking a traveling sales job. Since I once am again among the Vitamin-D-lacking office dwellers, I decided to get some advice from a successful road warrior, Dan. Currently a sales rep for a private Midwestern distributor, Dan is often on the road 3-4 days a week.

He also did not choose a Sebring convertible as his company car, so I figure he’s legit.

1. Travel Breaks Up the Routine, But it Can Be Draining

If you’re taking a sales job, be prepared to be flexible with your time—very, very flexible. While the 8-to-5 worker is on her way home after work, you can be stuck in an airport waiting on a delayed flight that won’t get in until midnight. “Be flexible,” says Dan. “By that, I mean be willing to get up at 3:30 AM on a Monday to catch a flight because the boss called on Friday afternoon saying he needs you to fly somewhere, and it’s urgent.” If you’re the one they hired to be on the road—well, it’s part of your job. 


2. Entertaining Can Be a Time Sucker

While you may score points with the client for playing a mean game of beer pong, all that fun often comes at the expense of your personal time—if you’re having drinks with the client, you sure aren’t grabbing drinks with your friends. You have to recognize this trade-off. (Dan says that he usually entertains clients about 5-6 hours per month, but sometimes it can be as much as 20.)

Plus, there’s always going to be a lot of behind-the-scenes work that goes into nailing down customer orders. Even when a sales call or meeting goes well, it won’t matter until you’ve got that signed order in hand.


3. You’re Only as Good as Your Current Numbers

In sales, you have targets. Monthly, quarterly, and annual targets. And meeting those sales numbers month after month can be stressful. Even if you had a great month in May, it won’t mean anything to the boss if you can’t keep that up in June. Consistency is important; otherwise it can look like you just got lucky a few times. Remember, since you rarely have face time with your boss, the only way he or she can judge your performance is by those numbers.

4. You’ll Have to Battle Stereotypes

Salespeople can get a bad rap, explains Dan. “Depending on the industry, salespeople can be perceived as dishonest.” Sometimes, despite Dan’s best efforts to build a rapport with a client, he still senses resistance. That’s where referrals come in handy, he says—it's important to always keep a close network of clients who can vouch for you. Also know that sincerity and honesty will pay off in the long run, and act accordingly. Customers can see right through the bull.

5. Get Used to Constant Change

The hardest part of sales, says Dan, is keeping up with the competition. There are always new products, technologies, and marketing strategies coming at you from all directions, compliments of your direct competitors. Plus, there’s a lot of information out there, and you’ll have to stay on your game if you’re going to be educating your customers about your product. In other words, you’ll need to be constantly educating yourself to keep up with the dynamic marketplace—and sometimes doing it on your own time.

A sales career can be an opportunity to work in a fast-paced, goal-oriented environment—but it’s definitely not all schmoozing over microbrews. Becoming a knowledgeable, trusted, and dynamic salesperson does take hard work. Keep this in mind, and you can give yourself a fantastic opportunity to control your own future—but first, my advice is to know what you’re getting into, and figure out if it’s a place you can thrive.

Photo courtesy of Jason Rogers.