How to Realize Your Dream of Working Remotely by Landing a Sales Job

How to Realize Your Dream of Working Remotely by Landing a Sales Job

Mike Monroe

Working remotely used to be the unicorn job. That was before Tim Ferriss, author of “The 4-Hour Workweek,” taught us that the primary barrier to entry for remote work wasn’t “there aren’t any remote positions available.” In fact, Gallup’s 2017 State of the American Workplace report revealed that 43 percent of working Americans were able to telecommute in 2016.

No, the primary barrier to entry to remote work for young people comes down to one thing: trust. The questions an employer has to answer are thus: Do I trust that this person will work? Do I trust that this person will perform without hand-holding? Do I trust that this person will fit with our organization’s systems for managing somebody remotely?

Want to prove you’re a good candidate for remote work? To cut your teeth in that environment, there’s no better profession in the world than sales.

Preparing Yourself for Sales

The first thing to know about sales is that it relies on performance-based incentives. (Yes, that means commission.) While the idea scares many, it won’t scare you if setting goals and taking responsibility runs in your blood. The very nature of commission is, “I don’t care how you do it, just get it done.” There’s nothing wrong with making a sale over the phone in your pajamas if you’re delivering knowledge and value to the customer.

That brings me to another point: In sales, communication trumps location. Sure, selling something 50 years ago meant being in front of the customer. But nowadays? Communication opportunities have expanded to include email, text and social media platforms.

Lastly, every sales position requires two things: sales training and sales management. Every successful sales organization in the world has these two structures in place. Sales training now encompasses video, audio, e-learning websites and even sophisticated learning management systems. A person’s ability to learn has never been less dependent on spending time in a (probably dingy) office cubicle.

Embracing Popular Channels

Today’s sales strategies encompass channels that simply didn’t exist even 30 years ago. Take text messages, for example. My wife and I just spent thousands of dollars (“These things cost how much?!”) purchasing new window treatments. But the “treatment specialist” working with us did what any good salesperson would: built value, showed us the spectrum of qualities and prices, and helped us find the best solution. And she did so while answering 95 percent of our questions via text.

If a salesperson’s top job is to build value, social media is the place to do it. I’m not talking about nonstop pitchfests on your personal accounts. Quite the opposite. Social selling is as much about selling yourself as it is selling a product. My company teaches representatives to be sales-focused on their accounts less than 20 percent of the time. The majority of their social media activity should be spent engaging with current customers.

Finally, as a guy who would rather write a nice, long email — that you probably wouldn’t want to read — the idea of making sales via phone always makes me smirk. But modern-day salespeople can connect quickly with customers while playing Frisbee in the park (bring headphones) or traveling someplace more fun than the shackled jobs their friends commonly work.

Landing a Remote Job

When you cross over to the land of remote work, you’ll never want to go back. Here are a few tips on how to find a remote sales position that’s a great fit for you and the company alike:

1. Polish your LinkedIn profile.

A quick search will turn up numerous articles on what a good LinkedIn profile looks like. If you don’t have one, make one. If your photo is blank or you haven’t taken the time to add meaningful connections, start by updating those areas. It’s perfectly acceptable for employers to look at your social profiles as part of the hiring process, so make yours stand out.

2. Hunt for opportunities on social media.

Use your social platforms — and I bet you have several — to help you find someone already working in remote sales. Start with your friends, then ask about their friends. Eventually, you’ll likely find someone with a remote position available. There’s a marketplace for students and recent graduates in many industries; companies want employees who are social, digitally savvy and eager to learn.

3. Consider direct sales.

No, I don’t mean pyramid schemes. I’m talking about companies that market products directly to customers rather than selling through a traditional storefront or on Amazon. In many industries, some of the highest-quality products require the personal touch of a salesperson. I’m talking about our window treatment specialist, the designer who sold us furniture and the estimator who sold us on his moving company — they all work remotely.

Make no mistake: I’m not saying breaking into sales is easy. But successful salespeople are ruined to “normal jobs” for the rest of their lives. Seriously. If you have the drive and dedication required, starting your career in remote work with sales is a no-brainer.

Mike Monroe is a Christian, husband, dad, marketer and wannabe athlete. Mike started working at Vector Marketing in 2000 as a student at Boston College. He wanted to stick out from the crowd and develop himself professionally. Nearly two decades later, that goal hasn’t changed. Learn more at

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